(E)-5-[1-Hy­droxy-3-(3,4,5-tri­meth­oxy­phen­yl)allyl­idene]-1,3-di­methyl­pyrimidine-2,4,6-trione: crystal structure and Hirshfeld surface analysis

Soto-Monsalve, M.; Romero, E.L.; Zuluaga, F.; Chaur, M.N.; D'Vries, R.F.

doi:10.1107/S2056989017010374

research communications

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ISSN: 2056-9890

Volume 73| Part 8| August 2017| Pages 1197-1201

https://doi.org/10.1107/S2056989017010374

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(E)-5-[1-Hydroxy-3-(3,4,5-trimethoxyphenyl)allylidene]-1,3-dimethylpyrimidine-2,4,6-trione: crystal structure and Hirshfeld surface analysis

Mónica Soto-Monsalve,^a Elkin L. Romero,^b Fabio Zuluaga,^b Manuel N. Chaur ^b and Richard F. D'Vries ^c ^*

^aInstituto de Química de São Carlos, Universidade de São Paulo 13566-590, São Carlos, Brazil, ^bDepartamento de Química, Universidad del Valle, AA 25360, Cali, Colombia, and ^cUniversidad Santiago de Cali, Calle 5 # 62-00, Cali, Colombia
^*Correspondence e-mail: richard.dvries00@usc.edu.co

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 19 May 2017; accepted 13 July 2017; online 18 July 2017)

In the title compound, C₁₈H₂₀N₂O₇, the dihedral angle between the aromatic rings is 7.28 (7)° and the almost planar conformation of the molecule is supported by an intramolecular O—H⋯O hydrogen bond, which closes an S(6) ring. In the crystal, weak C—H⋯O hydrogen bonds and aromatic π–π stacking link the molecules into a three-dimensional network. A Hirshfeld surface analysis showed that the major contribution to the intermolecular interactions are van der Waals interactions (H⋯H contacts), accounting for 48.4% of the surface.

Keywords: crystal structure; Hirshfeld surface; supramolecular structure; allylidene.

CCDC reference: 1562022

1. Chemical context

Bartituric acid derivatives are of interest due to their potential biological applications (Bojarski et al., 1985 ; Patrick, 2009 ). These compounds have materials science appplications due to the properties generated by π-conjugation, such as push–pull chromophores (Klikar et al., 2013 ; Seifert et al., 2012 ). The chemical structures of these derivatives show five potential metal-binding sites, which makes them versatile ligands for the construction of coordination and supramolecular compounds (Mahmudov et al., 2014 ), also important in organic synthesis, where they are largely used as substrates for Morita–Baylis–Hilmann and Diels–Alder reactions (Goswami & Das, 2009 ). Herein we report the crystal structure and Hisrshfeld surface analysis of (E)-5-[1-hydroxy-3-(3,4,5-trimethoxyphenyl)allylidene]-1,3-dimethylpyrimidine-2,4,6-trione (I), which presents potential applications in the study of the photophysical properties of different isomers for the development of supramolecular structures.

2. Structural commentary

The structure of (I), which crystallizes in the triclinic space group P $[\overline{1}]$ , presents conjugation over the C1—C10—C11—C12—C13 bonds, leading to a an almost planar conformation (Fig. 1); the C10—C11—C12—C13 and C1—C10—C11—C12 torsion angles are −176.76 (1) and −179.27 (1)°, respectively. The dihedral angle between the aromatic rings is 7.28 (7)°. The C atoms of the meta-methoxy groups lie close to the plane of their attached ring [deviations for atoms C7 and C9 of 0.289 (2) and 0.131 (2)Å, respectively], whereas the para-methoxy C atom deviates significantly, by 0.959 (2) Å, which is reflected in the C3—C4—O2—C8 torsion angle of 106.41 (19)°. An intramolecular O—H⋯O hydrogen bond (Table 1) closes an S(6) ring and a C—H⋯O interaction is also observed. A Mogul geometry check found that all the bond lengths and angles are within typical ranges (Bruno et al., 2004 ).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O5	0.82	1.74	2.4841 (15)	150
C11—H11⋯O7	0.93	2.16	2.8044 (18)	125
C8—H8B⋯O6ⁱ	0.96	2.60	3.341 (3)	135
C9—H9C⋯O7ⁱⁱ	0.96	2.42	3.3694 (19)	170
Symmetry codes: (i) x, y, z+1; (ii) -x-1, -y+1, -z+2.

Figure 1
The molecular structure of (I)

, showing 50% probability displacement ellipsoids.

3. Supramolecular features

The packing of the title compound features inversion dimers linked by pairs of C9—H9C⋯O7ⁱⁱ hydrogen bonds [C⋯O = 3.3694 (19) Å], which generate R₂²(24) loops. The dimers are linked along the [001] direction by the C8—H8B⋯O6ⁱ hydrogen bond [C⋯O = 3.341 (3) Å]. In addition, weak and very weak π–π interactions (which alternate with respect to the [010] direction) between benzene and pyrimidine rings [centroid–centroid separations = 3.8779 (1) and 4.2283 (9) Å, respectively] occur (Fig. 2). Together, these intermolecular interactions lead to a three-dimensional network (Fig. 3).

Figure 2
Details of the intermolecular interactions in the crystal of (I)

, showing (a) π–π stacking between rings 1 (N1/N2/C13–C16) and 2 (C1–C6) along the [010] direction, (b) an inversion dimer formed by the C9—H9C⋯O7ⁱⁱ hydrogen bond and (c) by the C8—H8B⋯O6ⁱ hydrogen bond. [Symmetry codes: (i) x, y, 1 + z; (ii) −1 − x, 1 − y, −z.]

Figure 3
Crystal packing representation of (I)

, viewed along the [010] direction.

4. Hirshfeld surfaces analysis

The Hirshfeld surface analysis shows the potential intermolecular contacts. Convex blue regions represent hydrogen-donor groups and concave red regions represent hydrogen-acceptor groups (Hirshfeld, 1977 ; McKinnon et al., 2004 ). In this case, the main donor groups are the methyl groups and the acceptor groups are the O atoms. The region of π–π interactions, observed as red and blue triangles over the aromatic rings, is also clear (Fig. 4). This surface confirms the importance of the interactions described previously.

Figure 4
Hirshfeld surface of the title compound as (a) shape index and (b) d_norm.

The two-dimensional fingerprint plot quantifies the contribution of each kind of interaction to the surface formation (McKinnon et al., 2007 ). For the title compound (Fig. 5), the major contribution is due to H⋯H corresponding to van der Waals interactions with 48.4% of the surface, followed by the O⋯H interaction, which contributes 26.5% (this contribution is observed as two sharp peaks in the plot); this behaviour is usual for strong hydrogen bonds (Spackman & McKinnon, 2002 ). Finally, π–π interactions represented by C⋯C interactions contribute 6.0% to the Hirshfeld surface.

Figure 5
Bidimensional fingerprint plots for the whole molecule and H⋯H, O⋯H, C⋯H, C⋯C and C⋯O close contacts.

5. Database survey

A general search in the Cambridge Structural Database (Groom et al., 2016 ) for barbituric acid derivatives yielded 718 hits. Limiting the search for a barbituric acid substituted at position C5 with a phenylpropyl group yielded 14 hits; two of these results present double-bond conjugation, namely 1,3-dibutyl-5-{3-[4-(dimethylamino)phenyl]prop-2-en-1-ylidene}pyrimidine-2,4,6(1H,3H,5H)-trione (Klikar et al., 2013) and 5-{3-[4-(dimethylamino)phenyl]prop-2-en-1-ylidene}pyrimidine-2,4,6(1H,3H,5H)-trione (Seifert et al., 2012).

6. Synthesis and crystallization

The title compound was prepared according to the literature procedure of Gorovoy et al. (2014 ). A mixture of 3,4,5-trimethoxybenzaldehyde and 5-acetyl-1,3-dimethylbarbituric acid was melted at 453 K and 2–3 drops of piperidine were added under constant stirring. After 5 min, the mixture solidified, providing a yellow powder, which was allowed to cool to room temperature. The solid residue was boiled in ethanol (20 ml) for a few minutes and the precipitate was filtered off by vacuum suction. The filtrate was left at room temperature, yielding yellow needles of the title compound after three weeks.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H-atom positions were calculated geometrically and refined using the riding model, with O—H = 0.82 Å, methyl C—H = 0.96 Å and aromatic C—H = 0.93 Å.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₈H₂₀N₂O₇
M_r	376.36
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	7.9989 (3), 8.0659 (3), 14.6533 (5)
α, β, γ (°)	104.520 (1), 98.422 (1), 98.909 (1)
V (Å³)	887.04 (6)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.11
Crystal size (mm)	1.07 × 0.33 × 0.28

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2015 )
T_min, T_max	0.714, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	26167, 3626, 3176
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.130, 1.04
No. of reflections	3626
No. of parameters	250
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.22
Computer programs: APEX2 and SAINT (Bruker, 2012 ), SHELXS2013 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ), Mercury (Macrae et al., 2008 ), CrystalExplorer (McKinnon et al., 2004), WinGX (Farrugia, 2012) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC reference: 1562022

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989017010374/hb7681sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017010374/hb7681Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), Mercury (Macrae et al., 2008) and CrystalExplorer (McKinnon et al., 2004); software used to prepare material for publication: WinGX (Farrugia, 2012) and OLEX2 (Dolomanov et al., 2009).

(E)-5-[1-Hydroxy-3-(3,4,5-trimethoxyphenyl)allylidene]-1,3-dimethylpyrimidine-2,4,6-trione top

Crystal data top

C₁₈H₂₀N₂O₇	Z = 2
M_r = 376.36	F(000) = 396
Triclinic, P1	D_x = 1.409 Mg m⁻³
a = 7.9989 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.0659 (3) Å	Cell parameters from 9895 reflections
c = 14.6533 (5) Å	θ = 2.6–26.4°
α = 104.520 (1)°	µ = 0.11 mm⁻¹
β = 98.422 (1)°	T = 296 K
γ = 98.909 (1)°	Needle, light yellow
V = 887.04 (6) Å³	1.07 × 0.33 × 0.28 mm

Data collection top

Bruker APEXII CCD diffractometer	3626 independent reflections
Radiation source: microfocus sealed X-ray tube	3176 reflections with I > 2σ(I)
Detector resolution: 7.9 pixels mm^-1	R_int = 0.021
φ and ω scans	θ_max = 26.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2015)	h = −10→9
T_min = 0.714, T_max = 0.745	k = −10→10
26167 measured reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.130	w = 1/[σ²(F_o²) + (0.0676P)² + 0.233P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3626 reflections	Δρ_max = 0.26 e Å⁻³
250 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
C1	0.10573 (17)	0.71389 (17)	1.15734 (9)	0.0393 (3)
C2	0.21740 (18)	0.71690 (18)	1.24039 (10)	0.0430 (3)
H2	0.3327	0.7711	1.2512	0.052*
C3	0.15737 (19)	0.63927 (18)	1.30710 (10)	0.0435 (3)
C4	−0.01447 (19)	0.55537 (18)	1.29072 (10)	0.0426 (3)
C5	−0.12826 (18)	0.55865 (19)	1.20923 (10)	0.0446 (3)
C6	−0.06846 (18)	0.63736 (18)	1.14315 (10)	0.0433 (3)
H6	−0.1446	0.6392	1.0892	0.052*
C7	0.4228 (3)	0.7414 (3)	1.41741 (15)	0.0841 (7)
H7A	0.4901	0.7025	1.3701	0.126*
H7B	0.4774	0.7334	1.4786	0.126*
H7C	0.4144	0.8605	1.4220	0.126*
C8	−0.1648 (3)	0.5368 (3)	1.41581 (15)	0.0809 (6)
H8A	−0.2713	0.5483	1.3805	0.121*
H8B	−0.1021	0.6501	1.4544	0.121*
H8C	−0.1886	0.4634	1.4567	0.121*
C9	−0.4173 (2)	0.4882 (3)	1.12169 (14)	0.0699 (5)
H9A	−0.3869	0.4312	1.0624	0.105*
H9B	−0.4172	0.6085	1.1248	0.105*
H9C	−0.5302	0.4314	1.1248	0.105*
C10	0.17536 (17)	0.78939 (18)	1.08679 (10)	0.0422 (3)
H10	0.2915	0.8426	1.1020	0.051*
C11	0.08636 (18)	0.78836 (19)	1.00250 (10)	0.0443 (3)
H11	−0.0303	0.7369	0.9863	0.053*
C12	0.16329 (17)	0.86397 (18)	0.93467 (10)	0.0426 (3)
C13	0.07305 (17)	0.87319 (17)	0.84766 (10)	0.0392 (3)
C14	0.16886 (19)	0.94308 (18)	0.78507 (11)	0.0441 (3)
C15	−0.0952 (2)	0.88897 (19)	0.66628 (11)	0.0480 (3)
C16	−0.11265 (18)	0.81213 (18)	0.81775 (10)	0.0417 (3)
C17	0.1805 (3)	1.0066 (3)	0.63158 (14)	0.0735 (5)
H17A	0.2704	1.1046	0.6673	0.110*
H17B	0.1053	1.0413	0.5856	0.110*
H17C	0.2307	0.9140	0.5986	0.110*
C18	−0.3720 (2)	0.7703 (3)	0.69641 (14)	0.0674 (5)
H18A	−0.3975	0.6558	0.6518	0.101*
H18B	−0.4164	0.8507	0.6656	0.101*
H18C	−0.4248	0.7668	0.7509	0.101*
N1	0.08167 (17)	0.94549 (16)	0.69760 (9)	0.0479 (3)
N2	−0.18496 (15)	0.82765 (16)	0.72844 (9)	0.0463 (3)
O1	0.25706 (15)	0.63579 (17)	1.39048 (8)	0.0625 (3)
O2	−0.06606 (16)	0.46212 (14)	1.35161 (8)	0.0573 (3)
O3	−0.29489 (14)	0.47840 (17)	1.20048 (9)	0.0638 (3)
O4	0.33028 (13)	0.92287 (18)	0.96038 (8)	0.0611 (3)
H4	0.3661	0.9594	0.9180	0.092*
O5	0.32765 (14)	1.00179 (16)	0.80691 (9)	0.0603 (3)
O6	−0.16669 (18)	0.89585 (18)	0.58887 (8)	0.0693 (4)
O7	−0.20868 (13)	0.75253 (17)	0.86397 (8)	0.0608 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0395 (7)	0.0408 (7)	0.0361 (6)	0.0050 (5)	0.0078 (5)	0.0095 (5)
C2	0.0369 (7)	0.0482 (7)	0.0415 (7)	0.0046 (5)	0.0054 (5)	0.0117 (6)
C3	0.0455 (8)	0.0483 (7)	0.0378 (7)	0.0118 (6)	0.0055 (6)	0.0141 (6)
C4	0.0482 (8)	0.0422 (7)	0.0418 (7)	0.0091 (6)	0.0138 (6)	0.0164 (6)
C5	0.0393 (7)	0.0475 (7)	0.0455 (7)	0.0016 (6)	0.0092 (6)	0.0143 (6)
C6	0.0398 (7)	0.0524 (8)	0.0367 (7)	0.0038 (6)	0.0047 (5)	0.0151 (6)
C7	0.0596 (11)	0.1186 (17)	0.0669 (12)	−0.0029 (11)	−0.0179 (9)	0.0429 (12)
C8	0.0891 (14)	0.1140 (17)	0.0749 (13)	0.0458 (13)	0.0456 (11)	0.0575 (12)
C9	0.0363 (8)	0.0968 (14)	0.0761 (12)	−0.0053 (8)	0.0029 (8)	0.0393 (10)
C10	0.0353 (7)	0.0473 (7)	0.0413 (7)	0.0018 (5)	0.0082 (5)	0.0111 (6)
C11	0.0350 (7)	0.0537 (8)	0.0424 (7)	−0.0011 (6)	0.0078 (5)	0.0159 (6)
C12	0.0327 (6)	0.0493 (7)	0.0448 (7)	0.0012 (5)	0.0100 (5)	0.0142 (6)
C13	0.0354 (7)	0.0428 (7)	0.0409 (7)	0.0038 (5)	0.0119 (5)	0.0142 (5)
C14	0.0444 (8)	0.0436 (7)	0.0504 (8)	0.0080 (6)	0.0194 (6)	0.0186 (6)
C15	0.0592 (9)	0.0477 (8)	0.0417 (7)	0.0173 (6)	0.0125 (6)	0.0150 (6)
C16	0.0370 (7)	0.0455 (7)	0.0425 (7)	0.0053 (5)	0.0085 (5)	0.0138 (6)
C17	0.0860 (13)	0.0876 (13)	0.0673 (11)	0.0165 (11)	0.0381 (10)	0.0456 (10)
C18	0.0459 (9)	0.0906 (13)	0.0620 (10)	0.0097 (8)	−0.0030 (8)	0.0244 (9)
N1	0.0586 (8)	0.0482 (7)	0.0462 (7)	0.0127 (5)	0.0216 (6)	0.0224 (5)
N2	0.0426 (7)	0.0535 (7)	0.0431 (6)	0.0096 (5)	0.0064 (5)	0.0152 (5)
O1	0.0543 (7)	0.0855 (8)	0.0517 (6)	0.0084 (6)	0.0002 (5)	0.0352 (6)
O2	0.0710 (7)	0.0561 (6)	0.0581 (7)	0.0159 (5)	0.0247 (6)	0.0309 (5)
O3	0.0423 (6)	0.0871 (8)	0.0622 (7)	−0.0093 (5)	0.0059 (5)	0.0370 (6)
O4	0.0330 (5)	0.0924 (9)	0.0565 (7)	−0.0072 (5)	0.0047 (5)	0.0324 (6)
O5	0.0428 (6)	0.0774 (8)	0.0696 (7)	0.0017 (5)	0.0222 (5)	0.0362 (6)
O6	0.0839 (9)	0.0855 (9)	0.0461 (6)	0.0249 (7)	0.0099 (6)	0.0284 (6)
O7	0.0348 (5)	0.0905 (8)	0.0591 (7)	−0.0065 (5)	0.0078 (5)	0.0369 (6)

Geometric parameters (Å, º) top

C1—C2	1.3926 (19)	C10—C11	1.330 (2)
C1—C6	1.3964 (19)	C10—H10	0.9300
C1—C10	1.4592 (19)	C11—C12	1.4509 (19)
C2—C3	1.389 (2)	C11—H11	0.9300
C2—H2	0.9300	C12—O4	1.3108 (17)
C3—O1	1.3668 (17)	C12—C13	1.395 (2)
C3—C4	1.392 (2)	C13—C14	1.4414 (18)
C4—O2	1.3713 (17)	C13—C16	1.4545 (19)
C4—C5	1.400 (2)	C14—O5	1.2484 (18)
C5—O3	1.3613 (17)	C14—N1	1.3728 (19)
C5—C6	1.3854 (19)	C15—O6	1.2115 (19)
C6—H6	0.9300	C15—N2	1.377 (2)
C7—O1	1.403 (2)	C15—N1	1.388 (2)
C7—H7A	0.9600	C16—O7	1.2171 (17)
C7—H7B	0.9600	C16—N2	1.3949 (18)
C7—H7C	0.9600	C17—N1	1.4651 (19)
C8—O2	1.397 (2)	C17—H17A	0.9600
C8—H8A	0.9600	C17—H17B	0.9600
C8—H8B	0.9600	C17—H17C	0.9600
C8—H8C	0.9600	C18—N2	1.464 (2)
C9—O3	1.427 (2)	C18—H18A	0.9600
C9—H9A	0.9600	C18—H18B	0.9600
C9—H9B	0.9600	C18—H18C	0.9600
C9—H9C	0.9600	O4—H4	0.8200

C2—C1—C6	119.47 (12)	C10—C11—H11	118.6
C2—C1—C10	118.69 (12)	C12—C11—H11	118.6
C6—C1—C10	121.83 (12)	O4—C12—C13	120.83 (12)
C3—C2—C1	120.32 (13)	O4—C12—C11	114.45 (12)
C3—C2—H2	119.8	C13—C12—C11	124.71 (12)
C1—C2—H2	119.8	C12—C13—C14	118.37 (12)
O1—C3—C2	124.48 (13)	C12—C13—C16	122.27 (12)
O1—C3—C4	115.30 (12)	C14—C13—C16	119.35 (13)
C2—C3—C4	120.22 (13)	O5—C14—N1	118.50 (12)
O2—C4—C3	119.14 (13)	O5—C14—C13	122.93 (14)
O2—C4—C5	121.34 (13)	N1—C14—C13	118.57 (13)
C3—C4—C5	119.39 (12)	O6—C15—N2	122.00 (15)
O3—C5—C6	124.28 (13)	O6—C15—N1	121.53 (15)
O3—C5—C4	115.49 (12)	N2—C15—N1	116.47 (13)
C6—C5—C4	120.22 (13)	O7—C16—N2	118.09 (13)
C5—C6—C1	120.23 (13)	O7—C16—C13	126.00 (13)
C5—C6—H6	119.9	N2—C16—C13	115.90 (12)
C1—C6—H6	119.9	N1—C17—H17A	109.5
O1—C7—H7A	109.5	N1—C17—H17B	109.5
O1—C7—H7B	109.5	H17A—C17—H17B	109.5
H7A—C7—H7B	109.5	N1—C17—H17C	109.5
O1—C7—H7C	109.5	H17A—C17—H17C	109.5
H7A—C7—H7C	109.5	H17B—C17—H17C	109.5
H7B—C7—H7C	109.5	N2—C18—H18A	109.5
O2—C8—H8A	109.5	N2—C18—H18B	109.5
O2—C8—H8B	109.5	H18A—C18—H18B	109.5
H8A—C8—H8B	109.5	N2—C18—H18C	109.5
O2—C8—H8C	109.5	H18A—C18—H18C	109.5
H8A—C8—H8C	109.5	H18B—C18—H18C	109.5
H8B—C8—H8C	109.5	C14—N1—C15	123.97 (12)
O3—C9—H9A	109.5	C14—N1—C17	118.57 (14)
O3—C9—H9B	109.5	C15—N1—C17	117.44 (14)
H9A—C9—H9B	109.5	C15—N2—C16	125.68 (13)
O3—C9—H9C	109.5	C15—N2—C18	116.73 (13)
H9A—C9—H9C	109.5	C16—N2—C18	117.58 (13)
H9B—C9—H9C	109.5	C3—O1—C7	117.14 (13)
C11—C10—C1	125.35 (13)	C4—O2—C8	116.71 (13)
C11—C10—H10	117.3	C5—O3—C9	117.32 (12)
C1—C10—H10	117.3	C12—O4—H4	109.5
C10—C11—C12	122.86 (13)

C6—C1—C2—C3	2.1 (2)	C16—C13—C14—N1	−1.7 (2)
C10—C1—C2—C3	−177.07 (13)	C12—C13—C16—O7	2.1 (2)
C1—C2—C3—O1	−179.95 (13)	C14—C13—C16—O7	−179.05 (15)
C1—C2—C3—C4	1.0 (2)	C12—C13—C16—N2	−179.24 (12)
O1—C3—C4—O2	−6.8 (2)	C14—C13—C16—N2	−0.35 (19)
C2—C3—C4—O2	172.34 (13)	O5—C14—N1—C15	−178.00 (13)
O1—C3—C4—C5	177.24 (13)	C13—C14—N1—C15	1.9 (2)
C2—C3—C4—C5	−3.6 (2)	O5—C14—N1—C17	3.8 (2)
O2—C4—C5—O3	6.2 (2)	C13—C14—N1—C17	−176.34 (14)
C3—C4—C5—O3	−177.92 (13)	O6—C15—N1—C14	179.01 (14)
O2—C4—C5—C6	−172.77 (13)	N2—C15—N1—C14	0.1 (2)
C3—C4—C5—C6	3.1 (2)	O6—C15—N1—C17	−2.7 (2)
O3—C5—C6—C1	−178.84 (14)	N2—C15—N1—C17	178.30 (14)
C4—C5—C6—C1	0.0 (2)	O6—C15—N2—C16	178.65 (14)
C2—C1—C6—C5	−2.7 (2)	N1—C15—N2—C16	−2.4 (2)
C10—C1—C6—C5	176.53 (13)	O6—C15—N2—C18	0.1 (2)
C2—C1—C10—C11	176.58 (14)	N1—C15—N2—C18	179.10 (14)
C6—C1—C10—C11	−2.6 (2)	O7—C16—N2—C15	−178.70 (14)
C1—C10—C11—C12	−179.27 (13)	C13—C16—N2—C15	2.5 (2)
C10—C11—C12—O4	4.4 (2)	O7—C16—N2—C18	−0.2 (2)
C10—C11—C12—C13	−176.76 (14)	C13—C16—N2—C18	−179.01 (14)
O4—C12—C13—C14	2.3 (2)	C2—C3—O1—C7	10.7 (2)
C11—C12—C13—C14	−176.48 (13)	C4—C3—O1—C7	−170.18 (17)
O4—C12—C13—C16	−178.81 (13)	C3—C4—O2—C8	106.41 (19)
C11—C12—C13—C16	2.4 (2)	C5—C4—O2—C8	−77.7 (2)
C12—C13—C14—O5	−2.9 (2)	C6—C5—O3—C9	−4.9 (2)
C16—C13—C14—O5	178.20 (13)	C4—C5—O3—C9	176.16 (15)
C12—C13—C14—N1	177.25 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O5	0.82	1.74	2.4841 (15)	150
C11—H11···O7	0.93	2.16	2.8044 (18)	125
C8—H8B···O6ⁱ	0.96	2.60	3.341 (3)	135
C9—H9C···O7ⁱⁱ	0.96	2.42	3.3694 (19)	170

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

Acknowledgements

ELR, FZ and MNC are grateful to the Vicerrectoría de Investigaciones and the Center of Excellence for Novel Materials (CENM) of the Universidad del Valle for the economic support to conduct this research. MSM and RD acknowledge FAPESP (2009/54011-8) for providing equipment, and Coordenação de Aperfeiçoamento de Pessoal de Nível Superior and Conselho Nacional de Desenvolvimento Cientifico e Tecnológico for the CNPq and CAPES/PNPD scholarships from the Brazilian Ministry of Education.

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