Cyclic trihydroxamic acid derivatives

In the crystal structures of two cyclic trihydroxamic acid derivatives containing the same substructure unit, viz. 1,3,5-trihydroxy-1,3,5-triazinane-2,4,6-trione dihydrate, C₃H₃N₃O₆·2H₂O, (I), and 1,3,5-benz­yloxy-1,3,5-triazinane-2,4,6-trione, C₂₄H₂₁N₃O₆, (II), there is no significant difference in the geometric parameters. In (I), there are 11 hydrogen bonds of the O—H...O type inter­connecting the mol­ecules in a three-dimensional network, while in (II) there are only two weak C—H...O hydrogen bonds. The results of IR spectroscopic analysis are in good agreement with the crystallographic study.

S1. Comment

The compound 1,3,5-trihydroxy-1,3,5-triazinane-2,4,6-trione has recently been applied as an aerobic oxidation catalyst (Hirai et al., 2003, 2004). Jadrijević-Mladar Takač et al. (2006 or 2004???) reported for it and its derivatives (acetyl and pivaloyl esters) physico-chemical analyses and properties such as pK_a, FT–IR, NMR, MS and TGA, and indicated some metal binding properties. Caira et al. (2006) investigated the ability of this compound to act as a host for a series of solvents. Among other triazinones and numerous cyclic amines, it has already been involved in the investigation of sulfur dioxide removal from fluids containing SO₂ (Christiansen et al. 1992). On the other hand, using pharmacophore query developed through a molecular modeling study of a class of known HIV-1 integrase inhibitors, the O-substituted derivative 1,3,5-trihydroxmethyl-1,3,5-triazinane-2,4,6-trione, has been observed as one of the four most potent candidates (IC50 < 30 µmol dm⁻³), with the triazinone molecule being a promising lead compound for the development of new anti-AIDS drugs.

Although the structure of 1,3,5-trihydroxy-1,3,5-triazinane-2,4,6-trione hosting three DMF molecules has already been published (Caira et al., 2006), no X-ray data for 1,3,5-trihydroxy-1,3,5-triazinane-2,4,6-trione dihydrate, (I), has been published so far. Therefore, as part of our work on the structure evaluation of hydroxamic acids (Matković-Čalogović et al., 2003; Đilović et al., 2006), in this paper we present the crystal structures of (I) and its precursor 1,3,5-benzyloxy-1,3,5-triazinane-2,4,6-trione, (II), as examples of unsubstituted and substituted cyclic trihydroxamic acids.

The molecular geometries and atom labelling schemes for (I) and (II) are shown in Figs. 1 and 2. There is no significant difference in the bond distances and angles in (I) and (II) (Tables 1 and 3). The geometric parameters are comparable to the corresponding values reported in the literature (Larsen, 1976; Đilović et al., 2006). The six-membered heterocyclic rings are almost planar [the largest displacements of the C and N atoms from the mean plane of triazine rings are, respectively, 0.031 (1) and 0.023 (1) Å for (I), and 0.024 (1) and 0.029 (1) Å for (II)] but show considerable deviation from the ideal hexagonal form. The internal C—N—C angles are considerably greater than 120° [the minimal and maximal values are 126.91 (10) and 128.05 (14)°], while the internal N—C—N angles are smaller than 120° [the minimum and maximum values are 111.94 (14) and 112.87 (10)°]. Thus, aromaticity is achieved only by the contribution of lone-pair electrons located at the N atoms.

The crystal packing of (I) is characterized by strong hydrogen-bonding interactions between the host and water molecules (Fig. 3 and Table 2). Voids in the crystal structure of the host molecule are occupied by water molecules which `transfer' the hydrogen-bond interactions throughout the crystal structure, interconnecting the molecules into an infinite three-dimensional framework.

Comparison of N,N',N''-tribenzyloxydicarbonimidic diamide (Đilović et al., 2006) with (II) reveals a difference in the crystal packing of two molecules containing the (CO)₂NOCH₂C₆H₅ substructure unit in non-cyclic and cyclic system, respectively. Because of the conformation, molecules of (II) are packed into `stepwise' chains with dominating weak hydrogen interactions (Fig. 4 and Table 4) and relatively close H···H contacts (2.283 Å). Chains parallel to the crystallographic plane (111) are connected through π–π (3.340 Å) and C—H···π interactions (2.891 Å). The presence of additional conformational freedom in the non-cyclic system results in sheets of centrosymmetric dimers, which are interconnected by strong hydrogen bonds. In addition to the above-mentioned interactions, C—H···π contacts between the terminal phenyl groups and weaker hydrogen interactions are also present in the crystal structure.

S2. Experimental

Compounds (I) and (II) were synthesized by the previously published procedure (Butula et al., 2000). The structure and purity was confirmed by means of thin layer chromatography, FT–IR and NMR analysis. Compound (I) was crystallized from a saturated acetone/diethyl ether (9:1) solution and (II) from a saturated acetone/diethyl ether (1:1) solution by slow evaporation at room temperature (a beaker containing the solution was covered with aluminium foil to slow down evaporation). Colorless crystals of good quality were obtained after three weeks, and these were stable for months when exposed to the atmosphere.

S3. Refinement

The positions of H atoms were obtained from a difference Fourier map and they were included in the refinement process with isotropic displacement parameters.

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2003) for (I); CrysAlis CCD (Oxford Diffraction,2003) for (II). For both compounds, cell refinement: CrysAlis CCD. Data reduction: CrysAlis CCD [or ERD?] (Oxford Diffraction, 2003) for (I); CrysAlis CCD [or RED?] (Oxford Diffraction,2003) for (II). For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006) for (I); ORTEP-3 (Farrugia, 1997) for (II). For both compounds, software used to prepare material for publication: PLATON (Spek, 2003).

Figures

	Fig. 1. A view of the molecular structure of (I), with the atom-labelling scheme. Displacement ellipsoids are shown at the 50% probability level.
	Fig. 2. A view of the molecular structure of (II), with the atom-labelling scheme. Displacement ellipsoids are shown at the 50% probability level.
	Fig. 3. The crystal packing of (I). Hydrogen bonds are indicated with dashed lines. Water molecules are represented in ball-and-stick style, while the other molecules are represented in capped sticks style. In the online version of the journal, all molecules are colored by symmetry equivalence. Difference between a and b?
	Fig. 4. The crystal packing of (II). Only one layer of molecules is shown. Hydrogen bonds are indicated with dashed lines.

(I) 1,3,5-trihydroxy-1,3,5-triazinane-2,4,6-trione dihydrate

Crystal data

C3H3N3O6·2H2O	Z = 4
Mr = 213.12	F(000) = 440
Monoclinic, P21/a	Dx = 1.953 Mg m^−3
Hall symbol: -P 2yab	Mo Kα radiation, λ = 0.71073 Å
a = 7.5109 (12) Å	µ = 0.20 mm^−1
b = 11.9244 (17) Å	T = 113 K
c = 8.1794 (12) Å	Prism, colourless
β = 98.405 (13)°	0.50 × 0.43 × 0.36 mm
V = 724.70 (19) Å^3

Data collection

Oxford Diffraction Xcalibur CCD diffractometer	1451 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
Graphite monochromator	θmax = 27.5°, θmin = 4.9°
ω scans	h = −9→9
4408 measured reflections	k = −15→14
1634 independent reflections	l = −10→10

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.088	All H-atom parameters refined
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0432P)^2 + 0.3604P] where P = (Fo^2 + 2Fc^2)/3
1634 reflections	(Δ/σ)max = 0.001
157 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

Experimental. The IR spectra were recorded on an FT–IR Perkin Elmer Paragon 500 spectrometer from samples dispersed in KBr pellets.

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
C1	0.36122 (16)	0.40859 (10)	0.89150 (15)	0.0139 (3)
C2	0.28211 (16)	0.48736 (11)	0.61008 (15)	0.0146 (3)
C3	0.46792 (16)	0.31608 (10)	0.65255 (14)	0.0135 (3)
N1	0.28310 (14)	0.48697 (9)	0.77898 (12)	0.0147 (2)
N2	0.37338 (14)	0.39749 (9)	0.55594 (12)	0.0144 (2)
N3	0.45038 (14)	0.32555 (9)	0.81811 (12)	0.0150 (2)
O1	0.35424 (12)	0.41340 (8)	1.03799 (11)	0.0168 (2)
H1O	0.106 (3)	0.5854 (19)	0.808 (3)	0.043 (6)*
O2	0.20627 (13)	0.55864 (8)	0.52094 (11)	0.0196 (2)
H2O	0.289 (3)	0.3624 (19)	0.343 (3)	0.043 (6)*
O3	0.55397 (12)	0.24296 (8)	0.59886 (11)	0.0179 (2)
H3O	0.482 (3)	0.1863 (18)	0.892 (3)	0.035 (5)*
O1N	0.22109 (13)	0.58290 (8)	0.84687 (11)	0.0192 (2)
O2N	0.38927 (13)	0.39594 (8)	0.38972 (10)	0.0162 (2)
O3N	0.53911 (13)	0.24573 (8)	0.92203 (11)	0.0173 (2)
O1W	0.11192 (14)	0.55977 (9)	0.18084 (12)	0.0209 (2)
H11W	0.190 (3)	0.5272 (19)	0.130 (3)	0.044 (6)*
H12W	0.152 (3)	0.5594 (18)	0.279 (3)	0.038 (5)*
O2W	0.40866 (13)	0.79979 (9)	0.73166 (12)	0.0194 (2)
H21W	0.437 (3)	0.7617 (19)	0.657 (3)	0.039 (5)*
H22W	0.405 (3)	0.756 (2)	0.805 (3)	0.044 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0128 (5)	0.0141 (6)	0.0146 (5)	−0.0028 (4)	0.0019 (4)	−0.0015 (4)
C2	0.0130 (5)	0.0170 (6)	0.0139 (6)	−0.0026 (5)	0.0023 (4)	−0.0001 (4)
C3	0.0135 (5)	0.0139 (6)	0.0131 (6)	−0.0040 (4)	0.0026 (4)	−0.0018 (4)
N1	0.0159 (5)	0.0156 (5)	0.0130 (5)	0.0024 (4)	0.0028 (4)	−0.0026 (4)
N2	0.0170 (5)	0.0170 (5)	0.0096 (5)	−0.0002 (4)	0.0031 (4)	−0.0006 (4)
N3	0.0182 (5)	0.0147 (5)	0.0117 (5)	0.0022 (4)	0.0012 (4)	0.0011 (4)
O1	0.0191 (5)	0.0202 (5)	0.0115 (4)	−0.0005 (3)	0.0031 (3)	−0.0009 (3)
O2	0.0214 (5)	0.0215 (5)	0.0154 (4)	0.0047 (4)	0.0015 (3)	0.0022 (4)
O3	0.0217 (5)	0.0175 (5)	0.0150 (4)	0.0021 (4)	0.0045 (3)	−0.0012 (3)
O1N	0.0195 (5)	0.0201 (5)	0.0182 (4)	0.0061 (4)	0.0031 (3)	−0.0038 (4)
O2N	0.0191 (5)	0.0219 (5)	0.0077 (4)	−0.0026 (4)	0.0029 (3)	−0.0012 (3)
O3N	0.0219 (5)	0.0153 (5)	0.0136 (4)	0.0026 (4)	−0.0020 (3)	0.0020 (3)
O1W	0.0247 (5)	0.0241 (5)	0.0138 (5)	0.0064 (4)	0.0029 (4)	−0.0006 (4)
O2W	0.0260 (5)	0.0187 (5)	0.0135 (5)	0.0046 (4)	0.0030 (4)	−0.0005 (4)

Geometric parameters (Å, º)

C1—O1	1.2084 (15)	N2—O2N	1.3822 (13)
C1—N1	1.3808 (16)	N3—O3N	1.3809 (13)
C1—N3	1.3814 (16)	O1N—H1O	0.88 (2)
C2—O2	1.2071 (16)	O2N—H2O	0.89 (2)
C2—N2	1.3802 (16)	O3N—H3O	0.84 (2)
C2—N1	1.3804 (16)	O1W—H11W	0.86 (3)
C3—O3	1.2063 (15)	O1W—H12W	0.82 (2)
C3—N2	1.3809 (16)	O2W—H21W	0.82 (2)
C3—N3	1.3843 (16)	O2W—H22W	0.80 (2)
N1—O1N	1.3825 (14)
C1—N1—O1N	115.33 (10)	N3—O3N—H3O	102.8 (14)
C1—N3—C3	127.27 (11)	O1—C1—N1	123.54 (11)
C2—N1—C1	127.48 (11)	O1—C1—N3	124.02 (11)
C2—N1—O1N	116.54 (10)	O2—C2—N1	122.65 (12)
C2—N2—C3	126.91 (10)	O2—C2—N2	124.47 (11)
C2—N2—O2N	116.42 (10)	O3—C3—N2	123.93 (11)
C3—N2—O2N	116.22 (10)	O3—C3—N3	123.25 (11)
N1—C1—N3	112.43 (10)	O3N—N3—C1	116.61 (10)
N1—O1N—H1O	104.9 (15)	O3N—N3—C3	116.04 (10)
N2—C2—N1	112.87 (10)	H11W—O1W—H12W	107 (2)
N2—C3—N3	112.80 (10)	H21W—O2W—H22W	104 (2)
N2—O2N—H2O	104.0 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1N—H1O···O1W^i	0.88 (2)	2.39 (2)	3.0060 (15)	127 (2)
O1N—H1O···O2W^ii	0.88 (2)	2.05 (2)	2.7758 (15)	140 (2)
O2N—H2O···O2W^iii	0.89 (2)	1.69 (2)	2.5803 (14)	175 (2)
O3N—H3O···O1W^iii	0.85 (2)	1.73 (2)	2.5754 (15)	173 (2)
O1W—H11W···O1^iv	0.86 (2)	2.05 (2)	2.8889 (15)	165 (2)
O1W—H11W···O1N^iv	0.86 (2)	2.45 (2)	2.9775 (14)	120 (2)
O1W—H12W···O2	0.82 (2)	1.96 (2)	2.7685 (14)	170 (2)
O2W—H21W···O2N^v	0.81 (2)	2.35 (2)	3.0294 (15)	141 (2)
O2W—H21W···O3^v	0.81 (2)	2.11 (2)	2.8052 (14)	144 (2)
O2W—H22W···O1N	0.80 (2)	2.54 (2)	3.1543 (15)	136 (2)
O2W—H22W···O3N^vi	0.80 (2)	2.21 (2)	2.8544 (14)	138 (2)

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

(II) 1,3,5-benzyloxy-1,3,5-triazinane-2,4,6-trione

Crystal data

C24H21N3O6	V = 1073.8 (5) Å^3
Mr = 447.44	Z = 2
Triclinic, P1	F(000) = 468
Hall symbol: -P 1	Dx = 1.384 Mg m^−3
a = 7.765 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.139 (3) Å	µ = 0.10 mm^−1
c = 12.783 (3) Å	T = 113 K
α = 66.36 (2)°	Prism, colourless
β = 76.78 (2)°	0.82 × 0.68 × 0.44 mm
γ = 82.79 (2)°

Data collection

Oxford Diffraction Xcalibur CCD diffractometer	3183 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 27.0°, θmin = 4.6°
ω scans	h = −9→9
8404 measured reflections	k = −15→15
4600 independent reflections	l = −16→16

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.167	All H-atom parameters refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.1119P)^2] where P = (Fo^2 + 2Fc^2)/3
4600 reflections	(Δ/σ)max < 0.001
382 parameters	Δρmax = 0.53 e Å^−3
0 restraints	Δρmin = −0.35 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
C1	0.8588 (2)	0.82131 (14)	0.06410 (14)	0.0220 (4)
C2	0.7641 (2)	1.03328 (15)	−0.04282 (14)	0.0230 (4)
C3	0.6172 (2)	0.92207 (15)	0.16315 (15)	0.0249 (4)
C11	0.9340 (2)	0.89208 (18)	−0.20064 (16)	0.0302 (4)
H11A	0.924 (3)	0.802 (2)	−0.1598 (17)	0.033 (5)*
H11B	0.817 (3)	0.9311 (18)	−0.2107 (17)	0.033 (5)*
C12	1.0661 (2)	0.92506 (16)	−0.31238 (15)	0.0260 (4)
C13	1.1794 (2)	0.84032 (19)	−0.34206 (18)	0.0337 (4)
H13	1.169 (3)	0.758 (2)	−0.2854 (18)	0.032 (5)*
C14	1.2971 (3)	0.8745 (2)	−0.44955 (19)	0.0401 (5)
H14	1.374 (3)	0.8143 (19)	−0.4721 (19)	0.041 (6)*
C15	1.3014 (2)	0.9929 (2)	−0.52610 (18)	0.0369 (5)
H15	1.385 (3)	1.017 (2)	−0.605 (2)	0.049 (6)*
C16	1.1900 (3)	1.07803 (19)	−0.49648 (17)	0.0358 (5)
H16	1.196 (3)	1.1678 (19)	−0.5558 (18)	0.034 (5)*
C17	1.0731 (2)	1.04489 (17)	−0.39132 (16)	0.0297 (4)
H17	0.992 (3)	1.101 (2)	−0.3667 (19)	0.041 (6)*
C21	0.6012 (2)	1.20535 (17)	0.08107 (19)	0.0305 (4)
H21A	0.695 (3)	1.2410 (18)	0.0214 (18)	0.031 (5)*
H21B	0.639 (3)	1.1573 (19)	0.1587 (19)	0.039 (5)*
C22	0.4584 (2)	1.29766 (15)	0.08718 (15)	0.0248 (4)
C23	0.3920 (2)	1.37283 (17)	−0.01112 (17)	0.0317 (4)
H23	0.445 (3)	1.3603 (18)	−0.0805 (18)	0.030 (5)*
C24	0.2580 (3)	1.45742 (17)	−0.0032 (2)	0.0398 (5)
H24	0.218 (3)	1.508 (2)	−0.075 (2)	0.063 (7)*
C25	0.1894 (3)	1.46835 (18)	0.1022 (2)	0.0410 (5)
H25	0.098 (3)	1.534 (2)	0.1043 (18)	0.041 (6)*
C26	0.2553 (3)	1.39466 (19)	0.1995 (2)	0.0391 (5)
H26	0.203 (3)	1.404 (2)	0.276 (2)	0.057 (7)*
C27	0.3877 (2)	1.30899 (17)	0.19298 (17)	0.0301 (4)
H27	0.427 (3)	1.2532 (19)	0.2657 (19)	0.038 (5)*
C31	0.8050 (3)	0.70820 (17)	0.33618 (17)	0.0322 (4)
H31A	0.755 (3)	0.7739 (19)	0.3628 (18)	0.033 (5)*
H31B	0.932 (3)	0.7212 (18)	0.2911 (18)	0.036 (5)*
C32	0.7795 (2)	0.58482 (15)	0.42814 (15)	0.0267 (4)
C33	0.6716 (2)	0.56619 (18)	0.53571 (16)	0.0321 (4)
H33	0.607 (3)	0.632 (2)	0.5504 (19)	0.043 (6)*
C34	0.6493 (3)	0.4502 (2)	0.61965 (18)	0.0412 (5)
H34	0.579 (3)	0.442 (2)	0.691 (2)	0.047 (6)*
C35	0.7336 (3)	0.35286 (19)	0.59678 (19)	0.0406 (5)
H35	0.724 (3)	0.272 (2)	0.652 (2)	0.053 (7)*
C36	0.8403 (3)	0.37212 (19)	0.4892 (2)	0.0403 (5)
H36	0.904 (3)	0.303 (2)	0.4707 (19)	0.044 (6)*
C37	0.8642 (2)	0.48661 (17)	0.40526 (17)	0.0327 (4)
H37	0.946 (3)	0.5002 (18)	0.3276 (19)	0.035 (5)*
N1	0.87062 (18)	0.93029 (13)	−0.03050 (12)	0.0239 (3)
N2	0.64202 (18)	1.02157 (12)	0.05813 (12)	0.0236 (3)
N3	0.72844 (18)	0.82497 (12)	0.15710 (12)	0.0243 (3)
O1	0.95215 (15)	0.73418 (11)	0.06547 (11)	0.0295 (3)
O2	0.77767 (17)	1.12336 (11)	−0.13051 (11)	0.0317 (3)
O3	0.51260 (16)	0.92042 (12)	0.24918 (11)	0.0329 (3)
O1N	1.00136 (14)	0.93721 (11)	−0.12697 (10)	0.0255 (3)
O2N	0.52359 (15)	1.11809 (10)	0.05381 (11)	0.0270 (3)
O3N	0.69860 (15)	0.71741 (10)	0.25166 (10)	0.0274 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0202 (8)	0.0242 (8)	0.0244 (8)	−0.0028 (6)	−0.0050 (6)	−0.0113 (7)
C2	0.0212 (8)	0.0253 (9)	0.0254 (9)	−0.0006 (6)	−0.0059 (7)	−0.0121 (7)
C3	0.0225 (8)	0.0268 (9)	0.0277 (9)	−0.0036 (7)	−0.0037 (7)	−0.0126 (7)
C11	0.0281 (9)	0.0392 (11)	0.0291 (10)	−0.0076 (8)	−0.0031 (7)	−0.0185 (8)
C12	0.0220 (8)	0.0338 (9)	0.0261 (9)	−0.0024 (7)	−0.0041 (7)	−0.0155 (7)
C13	0.0322 (10)	0.0356 (11)	0.0400 (11)	0.0037 (8)	−0.0119 (8)	−0.0203 (9)
C14	0.0259 (9)	0.0593 (14)	0.0491 (12)	0.0051 (9)	−0.0066 (9)	−0.0375 (12)
C15	0.0261 (9)	0.0577 (13)	0.0339 (11)	−0.0104 (9)	0.0006 (8)	−0.0258 (10)
C16	0.0373 (10)	0.0434 (12)	0.0289 (10)	−0.0132 (9)	−0.0034 (8)	−0.0144 (9)
C17	0.0287 (9)	0.0357 (10)	0.0298 (10)	−0.0018 (8)	−0.0048 (7)	−0.0180 (8)
C21	0.0229 (9)	0.0320 (10)	0.0450 (11)	−0.0004 (7)	−0.0061 (8)	−0.0241 (9)
C22	0.0197 (8)	0.0229 (8)	0.0327 (9)	−0.0035 (6)	−0.0020 (7)	−0.0125 (7)
C23	0.0298 (9)	0.0316 (10)	0.0346 (10)	−0.0051 (7)	−0.0062 (8)	−0.0127 (8)
C24	0.0373 (11)	0.0266 (10)	0.0513 (13)	−0.0031 (8)	−0.0185 (10)	−0.0050 (9)
C25	0.0297 (10)	0.0304 (10)	0.0695 (15)	0.0045 (8)	−0.0101 (10)	−0.0276 (10)
C26	0.0300 (10)	0.0473 (12)	0.0499 (12)	0.0000 (8)	−0.0016 (9)	−0.0326 (10)
C27	0.0277 (9)	0.0325 (10)	0.0311 (10)	−0.0031 (7)	−0.0024 (7)	−0.0145 (8)
C31	0.0383 (11)	0.0289 (10)	0.0306 (10)	−0.0066 (8)	−0.0121 (8)	−0.0082 (8)
C32	0.0268 (9)	0.0282 (9)	0.0243 (9)	−0.0035 (7)	−0.0081 (7)	−0.0070 (7)
C33	0.0291 (9)	0.0387 (11)	0.0299 (10)	−0.0006 (8)	−0.0058 (8)	−0.0148 (8)
C34	0.0346 (10)	0.0619 (14)	0.0240 (10)	−0.0179 (10)	−0.0018 (8)	−0.0108 (10)
C35	0.0396 (11)	0.0328 (11)	0.0423 (12)	−0.0109 (9)	−0.0181 (9)	0.0008 (9)
C36	0.0362 (11)	0.0331 (11)	0.0531 (13)	0.0022 (8)	−0.0158 (10)	−0.0154 (10)
C37	0.0289 (9)	0.0331 (10)	0.0345 (10)	−0.0014 (7)	−0.0033 (8)	−0.0131 (8)
N1	0.0213 (7)	0.0273 (8)	0.0226 (7)	−0.0011 (5)	0.0002 (6)	−0.0114 (6)
N2	0.0222 (7)	0.0212 (7)	0.0275 (7)	0.0030 (5)	−0.0050 (6)	−0.0106 (6)
N3	0.0242 (7)	0.0228 (7)	0.0230 (7)	−0.0004 (5)	−0.0029 (6)	−0.0067 (6)
O1	0.0283 (6)	0.0273 (7)	0.0347 (7)	0.0032 (5)	−0.0072 (5)	−0.0145 (5)
O2	0.0381 (7)	0.0281 (7)	0.0267 (7)	−0.0014 (5)	−0.0060 (5)	−0.0082 (6)
O3	0.0301 (7)	0.0374 (7)	0.0303 (7)	−0.0024 (5)	0.0021 (5)	−0.0160 (6)
O1N	0.0213 (6)	0.0336 (7)	0.0238 (6)	−0.0036 (5)	0.0007 (5)	−0.0154 (5)
O2N	0.0220 (6)	0.0243 (6)	0.0400 (7)	0.0049 (5)	−0.0085 (5)	−0.0182 (5)
O3N	0.0315 (7)	0.0249 (6)	0.0221 (6)	−0.0069 (5)	−0.0060 (5)	−0.0030 (5)

Geometric parameters (Å, º)

C1—O1	1.201 (2)	C22—C27	1.393 (3)
C1—N1	1.385 (2)	C23—C24	1.384 (3)
C1—N3	1.386 (2)	C23—H23	0.95 (2)
C2—O2	1.206 (2)	C24—C25	1.383 (3)
C2—N2	1.383 (2)	C24—H24	0.98 (3)
C2—N1	1.383 (2)	C25—C26	1.376 (3)
C3—O3	1.203 (2)	C25—H25	1.00 (2)
C3—N3	1.389 (2)	C26—C27	1.381 (3)
C3—N2	1.392 (2)	C26—H26	1.01 (3)
C11—O1N	1.474 (2)	C27—H27	0.99 (2)
C11—C12	1.493 (3)	C31—O3N	1.466 (2)
C11—H11A	1.01 (2)	C31—C32	1.490 (3)
C11—H11B	0.98 (2)	C31—H31A	0.99 (2)
C12—C13	1.382 (3)	C31—H31B	1.02 (2)
C12—C17	1.398 (3)	C32—C33	1.384 (3)
C13—C14	1.400 (3)	C32—C37	1.391 (3)
C13—H13	0.97 (2)	C33—C34	1.388 (3)
C14—C15	1.376 (3)	C33—H33	0.95 (2)
C14—H14	0.98 (2)	C34—C35	1.381 (3)
C15—C16	1.378 (3)	C34—H34	0.92 (2)
C15—H15	1.02 (2)	C35—C36	1.380 (3)
C16—C17	1.376 (3)	C35—H35	0.95 (3)
C16—H16	1.05 (2)	C36—C37	1.376 (3)
C17—H17	0.97 (2)	C36—H36	1.00 (2)
C21—O2N	1.469 (2)	C37—H37	1.01 (2)
C21—C22	1.486 (2)	O1N—N1	1.3872 (17)
C21—H21A	0.93 (2)	O2N—N2	1.3865 (17)
C21—H21B	1.02 (2)	O3N—N3	1.3789 (18)
C22—C23	1.391 (3)
O1—C1—N1	123.72 (15)	C23—C24—H24	116.3 (16)
O1—C1—N3	124.07 (15)	C26—C25—C24	119.65 (18)
N1—C1—N3	112.21 (14)	C26—C25—H25	121.5 (12)
O2—C2—N2	123.88 (15)	C24—C25—H25	118.7 (12)
O2—C2—N1	124.14 (15)	C25—C26—C27	120.48 (19)
N2—C2—N1	111.96 (14)	C25—C26—H26	118.4 (14)
O3—C3—N3	123.94 (16)	C27—C26—H26	121.1 (14)
O3—C3—N2	124.12 (15)	C26—C27—C22	120.31 (18)
N3—C3—N2	111.94 (14)	C26—C27—H27	118.8 (12)
O1N—C11—C12	105.94 (14)	C22—C27—H27	120.8 (12)
O1N—C11—H11A	108.6 (12)	O3N—C31—C32	105.74 (14)
C12—C11—H11A	111.5 (12)	O3N—C31—H31A	103.9 (12)
O1N—C11—H11B	107.2 (12)	C32—C31—H31A	114.5 (12)
C12—C11—H11B	112.9 (12)	O3N—C31—H31B	105.7 (11)
H11A—C11—H11B	110.5 (16)	C32—C31—H31B	112.8 (12)
C13—C12—C17	118.61 (17)	H31A—C31—H31B	113.1 (17)
C13—C12—C11	122.12 (17)	C33—C32—C37	119.40 (17)
C17—C12—C11	119.25 (16)	C33—C32—C31	121.07 (16)
C12—C13—C14	120.23 (19)	C37—C32—C31	119.52 (17)
C12—C13—H13	116.1 (12)	C32—C33—C34	119.93 (19)
C14—C13—H13	123.6 (12)	C32—C33—H33	120.1 (14)
C15—C14—C13	120.20 (18)	C34—C33—H33	119.9 (14)
C15—C14—H14	119.3 (13)	C35—C34—C33	120.6 (2)
C13—C14—H14	120.5 (13)	C35—C34—H34	122.2 (15)
C14—C15—C16	119.82 (19)	C33—C34—H34	117.2 (15)
C14—C15—H15	119.7 (13)	C36—C35—C34	119.16 (19)
C16—C15—H15	120.4 (13)	C36—C35—H35	117.8 (15)
C17—C16—C15	120.29 (19)	C34—C35—H35	123.0 (15)
C17—C16—H16	121.1 (11)	C37—C36—C35	120.9 (2)
C15—C16—H16	118.6 (11)	C37—C36—H36	118.4 (13)
C16—C17—C12	120.84 (17)	C35—C36—H36	120.7 (13)
C16—C17—H17	123.3 (13)	C36—C37—C32	120.04 (19)
C12—C17—H17	115.8 (13)	C36—C37—H37	120.4 (12)
O2N—C21—C22	105.83 (13)	C32—C37—H37	119.5 (12)
O2N—C21—H21A	109.2 (12)	N1—O1N—C11	109.33 (12)
C22—C21—H21A	109.5 (12)	N2—O2N—C21	109.90 (12)
O2N—C21—H21B	105.6 (12)	N3—O3N—C31	109.64 (12)
C22—C21—H21B	113.2 (12)	C2—N1—C1	128.05 (14)
H21A—C21—H21B	113.1 (17)	C2—N1—O1N	115.19 (13)
C23—C22—C27	118.98 (16)	C1—N1—O1N	116.72 (13)
C23—C22—C21	121.14 (17)	C2—N2—O2N	116.70 (13)
C27—C22—C21	119.87 (17)	C2—N2—C3	127.98 (14)
C24—C23—C22	120.14 (19)	O2N—N2—C3	115.24 (13)
C24—C23—H23	124.8 (12)	O3N—N3—C1	115.89 (13)
C22—C23—H23	115.1 (12)	O3N—N3—C3	116.35 (13)
C25—C24—C23	120.43 (19)	C1—N3—C3	127.62 (14)
C25—C24—H24	123.3 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O3^i	1.02 (2)	2.54 (2)	3.350 (3)	136 (2)
C25—H25···O1^ii	1.00 (3)	2.46 (3)	3.423 (3)	161 (2)

Symmetry codes: (i) x+1, y, z−1; (ii) x−1, y+1, z.