research communications
RS,21SR,22RS,24SR)-28-oxo-24-propyl-8,11,14-trioxa-24,27-diazapentacyclo[19.5.1.122,26.02,7.015,20]octacosa-2,4,6,15(20),16,18-hexaene acetic acid monosolvate
of (1aInstitute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Hanoi, Vietnam, bDepartment of Chemistry, Vietnam National University, 144 Xuan Thuy, Cau Giay, Hanoi, Vietnam, cOrganic Chemistry Department, Peoples' Friendship University of Russia, 6 Miklukho-Maklay St., Moscow 117198, Russian Federation, dInorganic Chemistry Department, Peoples' Friendship University of Russia, 6 Miklukho-Maklay St, Moscow, 117198, Russian Federation, and eX-Ray Structural Centre, A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St, B-334, Moscow 119991, Russian Federation
*Correspondence e-mail: thh1101@yahoo.com
The title compound, C26H32N2O4(M)·C2H4O2, (I), is the product of the Petrenko–Kritchenko condensation of N-propylpiperidinone with 1,5-bis(2-formylphenoxy)-3-oxapentane and ammonium acetate. In M, the aza-14-crown-3-ether ring adopts a bowl conformation, with the configuration of the C—O—C—C —O—C—C—O—C polyether chain being t–g(−)–t–t–g(+)–t (t = trans, 180°; g = gauche, ±60°). The dihedral angle between the planes of the benzene rings fused to the aza-14-crown-4-ether moiety is 62.75 (5)°. The central piperidinone ring has a boat conformation, whereas the terminal piperidinone ring adopts a chair conformation. The boat conformation of the central piperidinone ring is supported by the bifurcated intramolecular N—H⋯O hydrogen bond. In the crystal, each solvent molecule is linked to molecule M via strong O—H⋯N hydrogen bonding, forming hydrogen-bonded pairs of molecules, which further interact through weak C—H⋯O hydrogen bonds, forming layers parallel to the ac plane.
CCDC reference: 1478354
1. Chemical context
The design, synthesis and applications of macrocyclic ligands for coordination and supramolecular chemistry have attracted very great attention from investigators over the last several decades (Hiraoka, 1978; Pedersen, 1988; Schwan & Warkentin, 1988; Gokel & Murillo, 1996; Bradshaw & Izatt, 1997). Recently, we have developed effective methods of synthesis of azacrown containing piperidine (Levov et al., 2006, 2008; Anh et al., 2008, 2012a,b,c; Hieu et al. (2012a,b, 2013), perhydropyrimidine (Hieu et al., 2011), perhydrotriazine (Khieu et al., 2011) and bispidine (Komarova et al., 2008; Sokol et al., 2011) subunits.
In attempts to apply this chemistry to obtain a macrocyclic ligand containing the N-propylsubstituted bispidine moiety, we studied the Petrenko–Kritchenko condensation of N-propylpiperidinone with 1,5-bis(2-formylphenoxy)-3-oxapentane and ammonium acetate. The reaction proceeded smoothly to give the expected azacrown system with a high yield of 73% (Fig. 1).
The prepared compound was studied by X-ray 26H32N2O4(M)·C2H4O2, (I) (Fig. 2). This finding seems to show the possibility of forming the second piperidine ring by the direct participation of the ammonium ion without the loss of its counter-ionic nature.
It is a stable complex and crystallized as an acetic acid monosolvate, C2. Structural commentary
The molecule of M forms a robust hydrogen-bonded complex with an acetic acid molecule by a strong intermolecular O—H⋯N hydrogen bond (Fig. 2 and Table 1). The molecule of M comprises a fused pentacyclic system containing the aza-14-crown-3-ether macrocycle, two piperidinone and two benzene rings (Fig. 2). The aza-14-crown-3-ether ring adopts a bowl conformation. The conformation of the C7—O8—C9—C10 —O11—C12—C13—O14—C15 polyether chain is t–g(−)–t–t–g(+)–t (t = trans, 180°; g = gauche, ±60°). The dihedral angle between the planes of the benzene rings fused to the aza-14-crown-4-ether moiety is 62.75 (5)°. The central piperidinone ring has a boat conformation, whereas the terminal piperidinone ring adopts a chair conformation. Apparently, the conformation of the central piperidinone ring is determined by the bifurcated intramolecular N—H⋯O hydrogen bond (Fig. 2 and Table 1). Both nitrogen atoms N25 and N27 have a trigonal–pyramidal geometry (the sums of the bond angles are 326.9 and 335.2°, respectively). The bulk propyl substituent at the nitrogen atom N27 occupies the more favourable equatorial position.
The molecule of M possesses four asymmetric centers at the C1, C21, C22 and C24 carbon atoms and can have potentially numerous The crystal of (I) is racemic and consists of enantiomeric pairs of M with the following of the centers: rac-1R*, 21S*,22R*,24S*.
3. Supramolecular features
In the crystal, the hydrogen-bonded complex (I) forms centrosymmetric dimers by C—H⋯O hydrogen bonds (Fig. 3 and Table 1). The dimers interact through weak C—H⋯O hydrogen bonds, forming layers parallel to ac plane (Fig. 4 and Table 1).
4. Synthesis and crystallization
1,5-Bis(2-formyl-phenoxy)-3-oxapentane was synthesized according to the procedure described previously (Levov et al., 2008) and purified by recrystallization in ethanol.
Ammonium acetate (3.0 g, 39 mmol) was added to a solution of 1,5-bis(2-formyl- phenoxy)-3-oxapentane (3.14 g, 10.0 mmol) and N-propylpiperidone (1.41 g, 10.0 mmol) in ethanol (30 mL) mixed with acetic acid (1 mL). The reaction mixture was stirred at 293 K for 3 d (monitoring by TLC until disappearance of the starting heterocyclic ketone spot). At the end of the reaction, the formed precipitate was filtered off, washed with ethanol and recrystallized from ethanol to give 3.60 g of colourless block-like crystals of (I) (yield 73%; m.p. = 490–492 K).
IR (KBr), ν/cm−1: 1602, 1728, 3263, 3463. 1H NMR (CDCl3, 400 MHz, 300 K): δ = 1.08 (t, 3H, CH3, J = 6.7), 1.25 (m, 2H, CH2CH2CH3), 1.61 (m, 2H, NCH2CH2), 1.83 (s, 3H, s, 3H, CH3COO−), 2.49 (m, 4H, 2H23 and 2H25), 2.76 (m, 2H, H22 and H26), 3.12 (br m, 1H, NH), 3.86–4.10 (m, 8H, OCH2CH2OCH2CH2O), 4.83 (m, 2H, H1 and H21), 6.78–6.86 (m, 4H, Harom), 7.25–7.41 (m, 4H, Harom). 13C NMR (CDCl3, 80 MHz, 300 K): δ = 12.3 (CH3), 21.2 (CH2), 22.6 (CH2), 54.4 (CH2), 57.7 (CH2), 60.5 (CH2), 64.3 (CH2), 67.0 (CH), 79.1 (CH), 111.5 (Carom), 121.1 (Carom), 129.1 (Carom), 131.8 (Carom), 175.7 C=O). Analysis calculated for C28H36N2O6: C, 67.72; H, 7.31; N, 5.64. Found: C, 67.54; H, 7.42; N, 5.41.
5. details
Crystal data, data collection and structure . The hydrogen atoms of the amino and hydroxy groups were localized in the difference-Fourier maps and included in the with fixed positional (using a riding model) and isotropic displacement parameters [Uiso(H) = 1.2Ueq(N) and 1.5Ueq(O)]. The other hydrogen atoms were placed in calculated positions with C—H = 0.95–1.00 Å and refined in the riding model with fixed isotropic displacement parameters [Uiso(H) = 1.5Ueq(C) for the methyl group and 1.2Ueq(C) for the other groups].
details are summarized in Table 2
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Supporting information
CCDC reference: 1478354
https://doi.org/10.1107/S2056989016007556/cv5505sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016007556/cv5505Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989016007556/cv5505Isup3.cml
Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C26H32N2O4·C2H4O2 | Z = 2 |
Mr = 496.59 | F(000) = 532 |
Triclinic, P1 | Dx = 1.267 Mg m−3 |
a = 9.4610 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.673 (1) Å | Cell parameters from 3303 reflections |
c = 12.9862 (11) Å | θ = 2.4–29.1° |
α = 83.780 (2)° | µ = 0.09 mm−1 |
β = 79.998 (2)° | T = 120 K |
γ = 67.335 (2)° | Prism, colourless |
V = 1301.95 (19) Å3 | 0.30 × 0.20 × 0.20 mm |
Bruker APEXII CCD diffractometer | 5223 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.046 |
φ and ω scans | θmax = 30.6°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −13→13 |
Tmin = 0.946, Tmax = 0.963 | k = −16→16 |
17314 measured reflections | l = −18→18 |
7954 independent reflections |
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.065 | Hydrogen site location: mixed |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0492P)2 + 0.4449P] where P = (Fo2 + 2Fc2)/3 |
7954 reflections | (Δ/σ)max = 0.001 |
327 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.7020 (2) | 0.80143 (16) | 0.32331 (13) | 0.0151 (3) | |
H1 | 0.5943 | 0.8030 | 0.3432 | 0.018* | |
C2 | 0.7882 (2) | 0.73774 (16) | 0.41389 (13) | 0.0156 (3) | |
C3 | 0.7109 (2) | 0.70361 (17) | 0.50551 (14) | 0.0187 (4) | |
H3 | 0.6039 | 0.7188 | 0.5099 | 0.022* | |
C4 | 0.7870 (2) | 0.64764 (17) | 0.59081 (14) | 0.0219 (4) | |
H4 | 0.7321 | 0.6262 | 0.6534 | 0.026* | |
C5 | 0.9433 (2) | 0.62344 (17) | 0.58399 (14) | 0.0217 (4) | |
H5 | 0.9957 | 0.5846 | 0.6421 | 0.026* | |
C6 | 1.0246 (2) | 0.65524 (16) | 0.49323 (14) | 0.0199 (4) | |
H6 | 1.1322 | 0.6374 | 0.4887 | 0.024* | |
C7 | 0.9465 (2) | 0.71355 (16) | 0.40895 (14) | 0.0171 (3) | |
O8 | 1.01351 (14) | 0.75192 (12) | 0.31660 (10) | 0.0216 (3) | |
C9 | 1.1750 (2) | 0.73063 (18) | 0.30576 (15) | 0.0212 (4) | |
H9A | 1.2378 | 0.6404 | 0.3071 | 0.025* | |
H9B | 1.1961 | 0.7677 | 0.3636 | 0.025* | |
C10 | 1.2134 (2) | 0.79095 (18) | 0.20263 (15) | 0.0236 (4) | |
H10A | 1.1391 | 0.8779 | 0.1975 | 0.028* | |
H10B | 1.3188 | 0.7918 | 0.1963 | 0.028* | |
O11 | 1.20538 (16) | 0.72247 (12) | 0.12144 (10) | 0.0241 (3) | |
C12 | 1.1807 (2) | 0.79105 (18) | 0.02482 (15) | 0.0244 (4) | |
H12A | 1.2802 | 0.7912 | −0.0144 | 0.029* | |
H12B | 1.1104 | 0.8782 | 0.0374 | 0.029* | |
C13 | 1.1102 (2) | 0.73105 (19) | −0.03698 (15) | 0.0240 (4) | |
H13A | 1.1011 | 0.7713 | −0.1079 | 0.029* | |
H13B | 1.1748 | 0.6416 | −0.0437 | 0.029* | |
O14 | 0.95979 (15) | 0.74700 (12) | 0.01989 (10) | 0.0232 (3) | |
C15 | 0.8744 (2) | 0.69058 (16) | −0.01385 (14) | 0.0194 (4) | |
C16 | 0.9239 (2) | 0.61671 (17) | −0.10028 (14) | 0.0226 (4) | |
H16 | 1.0216 | 0.6039 | −0.1414 | 0.027* | |
C17 | 0.8277 (2) | 0.56197 (18) | −0.12541 (15) | 0.0258 (4) | |
H17 | 0.8612 | 0.5108 | −0.1838 | 0.031* | |
C18 | 0.6844 (2) | 0.58076 (18) | −0.06688 (15) | 0.0256 (4) | |
H18 | 0.6194 | 0.5435 | −0.0851 | 0.031* | |
C19 | 0.6368 (2) | 0.65503 (17) | 0.01915 (14) | 0.0215 (4) | |
H19 | 0.5384 | 0.6682 | 0.0595 | 0.026* | |
C20 | 0.7302 (2) | 0.71058 (16) | 0.04736 (13) | 0.0166 (3) | |
C21 | 0.6760 (2) | 0.78938 (16) | 0.14221 (13) | 0.0152 (3) | |
H21 | 0.5681 | 0.7948 | 0.1691 | 0.018* | |
C22 | 0.6672 (2) | 0.92585 (16) | 0.11686 (14) | 0.0166 (3) | |
H22 | 0.7129 | 0.9357 | 0.0426 | 0.020* | |
C23 | 0.7502 (2) | 0.96020 (16) | 0.19043 (14) | 0.0173 (4) | |
O23 | 0.84543 (15) | 1.00757 (12) | 0.16251 (10) | 0.0237 (3) | |
C24 | 0.6875 (2) | 0.93985 (16) | 0.30267 (14) | 0.0166 (3) | |
H24 | 0.7460 | 0.9601 | 0.3505 | 0.020* | |
N25 | 0.76982 (17) | 0.72799 (13) | 0.22760 (11) | 0.0149 (3) | |
H25 | 0.8675 | 0.7259 | 0.2065 | 0.018* | |
C26 | 0.4975 (2) | 1.01694 (17) | 0.13699 (14) | 0.0191 (4) | |
H26A | 0.4925 | 1.1032 | 0.1216 | 0.023* | |
H26B | 0.4366 | 1.0002 | 0.0898 | 0.023* | |
N27 | 0.43102 (17) | 1.00357 (14) | 0.24556 (11) | 0.0173 (3) | |
C28 | 0.5164 (2) | 1.02988 (17) | 0.31802 (14) | 0.0187 (4) | |
H28A | 0.4688 | 1.0206 | 0.3910 | 0.022* | |
H28B | 0.5107 | 1.1166 | 0.3054 | 0.022* | |
C29 | 0.2644 (2) | 1.07837 (17) | 0.26161 (15) | 0.0208 (4) | |
H29A | 0.2169 | 1.0627 | 0.2052 | 0.025* | |
H29B | 0.2495 | 1.1674 | 0.2557 | 0.025* | |
C30 | 0.1803 (2) | 1.05181 (18) | 0.36677 (16) | 0.0244 (4) | |
H30A | 0.2005 | 1.0930 | 0.4222 | 0.029* | |
H30B | 0.2199 | 0.9612 | 0.3837 | 0.029* | |
C31 | 0.0058 (2) | 1.0991 (2) | 0.36409 (18) | 0.0352 (5) | |
H31A | −0.0476 | 1.0901 | 0.4344 | 0.053* | |
H31B | −0.0152 | 1.0506 | 0.3158 | 0.053* | |
H31C | −0.0314 | 1.1869 | 0.3404 | 0.053* | |
O32 | 0.75677 (15) | 0.50970 (13) | 0.27083 (11) | 0.0263 (3) | |
H32 | 0.7652 | 0.5868 | 0.2569 | 0.039* | |
O33 | 0.51282 (18) | 0.61820 (16) | 0.33797 (16) | 0.0489 (5) | |
C32 | 0.6186 (2) | 0.5196 (2) | 0.31786 (19) | 0.0335 (5) | |
C33 | 0.6036 (3) | 0.3964 (3) | 0.3473 (3) | 0.0692 (10) | |
H33A | 0.5385 | 0.4009 | 0.4154 | 0.104* | |
H33B | 0.7064 | 0.3320 | 0.3516 | 0.104* | |
H33C | 0.5561 | 0.3759 | 0.2942 | 0.104* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0143 (8) | 0.0166 (8) | 0.0132 (8) | −0.0045 (7) | −0.0020 (6) | −0.0009 (6) |
C2 | 0.0168 (8) | 0.0149 (8) | 0.0142 (8) | −0.0040 (7) | −0.0046 (7) | −0.0011 (6) |
C3 | 0.0187 (9) | 0.0212 (9) | 0.0175 (9) | −0.0094 (7) | −0.0024 (7) | 0.0006 (7) |
C4 | 0.0291 (10) | 0.0221 (9) | 0.0147 (8) | −0.0102 (8) | −0.0041 (7) | 0.0025 (7) |
C5 | 0.0282 (10) | 0.0178 (9) | 0.0189 (9) | −0.0050 (8) | −0.0123 (8) | 0.0015 (7) |
C6 | 0.0181 (9) | 0.0183 (9) | 0.0222 (9) | −0.0030 (7) | −0.0077 (7) | −0.0024 (7) |
C7 | 0.0181 (9) | 0.0166 (8) | 0.0161 (8) | −0.0052 (7) | −0.0031 (7) | −0.0023 (7) |
O8 | 0.0138 (6) | 0.0316 (7) | 0.0192 (6) | −0.0089 (6) | −0.0033 (5) | 0.0025 (6) |
C9 | 0.0120 (8) | 0.0273 (10) | 0.0250 (10) | −0.0068 (7) | −0.0031 (7) | −0.0051 (8) |
C10 | 0.0166 (9) | 0.0253 (10) | 0.0305 (10) | −0.0103 (8) | −0.0002 (8) | −0.0037 (8) |
O11 | 0.0293 (8) | 0.0220 (7) | 0.0208 (7) | −0.0099 (6) | −0.0040 (6) | 0.0011 (6) |
C12 | 0.0186 (9) | 0.0263 (10) | 0.0253 (10) | −0.0085 (8) | 0.0004 (8) | 0.0062 (8) |
C13 | 0.0179 (9) | 0.0302 (10) | 0.0186 (9) | −0.0068 (8) | 0.0044 (7) | 0.0009 (8) |
O14 | 0.0183 (7) | 0.0290 (7) | 0.0226 (7) | −0.0103 (6) | 0.0037 (5) | −0.0076 (6) |
C15 | 0.0238 (10) | 0.0161 (8) | 0.0164 (8) | −0.0053 (7) | −0.0042 (7) | 0.0001 (7) |
C16 | 0.0274 (10) | 0.0201 (9) | 0.0139 (8) | −0.0031 (8) | −0.0008 (7) | 0.0002 (7) |
C17 | 0.0395 (12) | 0.0206 (9) | 0.0148 (9) | −0.0068 (9) | −0.0072 (8) | −0.0015 (7) |
C18 | 0.0344 (11) | 0.0219 (9) | 0.0226 (10) | −0.0101 (9) | −0.0092 (9) | −0.0025 (8) |
C19 | 0.0242 (10) | 0.0210 (9) | 0.0205 (9) | −0.0085 (8) | −0.0068 (8) | 0.0006 (7) |
C20 | 0.0197 (9) | 0.0171 (8) | 0.0123 (8) | −0.0048 (7) | −0.0055 (7) | 0.0006 (7) |
C21 | 0.0131 (8) | 0.0183 (8) | 0.0143 (8) | −0.0057 (7) | −0.0032 (6) | 0.0002 (7) |
C22 | 0.0170 (8) | 0.0159 (8) | 0.0153 (8) | −0.0040 (7) | −0.0041 (7) | 0.0010 (7) |
C23 | 0.0156 (8) | 0.0121 (8) | 0.0215 (9) | −0.0020 (7) | −0.0043 (7) | 0.0009 (7) |
O23 | 0.0236 (7) | 0.0240 (7) | 0.0266 (7) | −0.0129 (6) | −0.0044 (6) | 0.0033 (6) |
C24 | 0.0152 (8) | 0.0168 (8) | 0.0172 (8) | −0.0041 (7) | −0.0043 (7) | −0.0025 (7) |
N25 | 0.0134 (7) | 0.0183 (7) | 0.0119 (7) | −0.0047 (6) | −0.0023 (5) | 0.0004 (6) |
C26 | 0.0189 (9) | 0.0189 (9) | 0.0169 (9) | −0.0035 (7) | −0.0054 (7) | 0.0006 (7) |
N27 | 0.0144 (7) | 0.0186 (7) | 0.0160 (7) | −0.0021 (6) | −0.0035 (6) | −0.0021 (6) |
C28 | 0.0181 (9) | 0.0171 (8) | 0.0185 (9) | −0.0031 (7) | −0.0040 (7) | −0.0026 (7) |
C29 | 0.0160 (9) | 0.0187 (9) | 0.0242 (9) | −0.0018 (7) | −0.0035 (7) | −0.0037 (7) |
C30 | 0.0191 (9) | 0.0236 (10) | 0.0287 (10) | −0.0069 (8) | 0.0011 (8) | −0.0055 (8) |
C31 | 0.0198 (10) | 0.0460 (13) | 0.0418 (13) | −0.0136 (10) | 0.0039 (9) | −0.0197 (11) |
O32 | 0.0226 (7) | 0.0234 (7) | 0.0322 (8) | −0.0096 (6) | −0.0017 (6) | 0.0025 (6) |
O33 | 0.0194 (8) | 0.0413 (10) | 0.0799 (14) | −0.0085 (8) | −0.0020 (8) | 0.0035 (9) |
C32 | 0.0218 (10) | 0.0343 (12) | 0.0450 (13) | −0.0121 (10) | −0.0105 (10) | 0.0106 (10) |
C33 | 0.0372 (15) | 0.0426 (15) | 0.129 (3) | −0.0252 (13) | −0.0097 (17) | 0.0252 (18) |
C1—N25 | 1.490 (2) | C19—C20 | 1.394 (2) |
C1—C2 | 1.510 (2) | C19—H19 | 0.9500 |
C1—C24 | 1.565 (2) | C20—C21 | 1.513 (2) |
C1—H1 | 1.0000 | C21—N25 | 1.487 (2) |
C2—C3 | 1.389 (2) | C21—C22 | 1.564 (2) |
C2—C7 | 1.404 (2) | C21—H21 | 1.0000 |
C3—C4 | 1.389 (2) | C22—C23 | 1.508 (2) |
C3—H3 | 0.9500 | C22—C26 | 1.542 (2) |
C4—C5 | 1.383 (3) | C22—H22 | 1.0000 |
C4—H4 | 0.9500 | C23—O23 | 1.215 (2) |
C5—C6 | 1.389 (3) | C23—C24 | 1.505 (2) |
C5—H5 | 0.9500 | C24—C28 | 1.545 (2) |
C6—C7 | 1.392 (2) | C24—H24 | 1.0000 |
C6—H6 | 0.9500 | N25—H25 | 0.9090 |
C7—O8 | 1.371 (2) | C26—N27 | 1.459 (2) |
O8—C9 | 1.434 (2) | C26—H26A | 0.9900 |
C9—C10 | 1.499 (3) | C26—H26B | 0.9900 |
C9—H9A | 0.9900 | N27—C28 | 1.466 (2) |
C9—H9B | 0.9900 | N27—C29 | 1.468 (2) |
C10—O11 | 1.419 (2) | C28—H28A | 0.9900 |
C10—H10A | 0.9900 | C28—H28B | 0.9900 |
C10—H10B | 0.9900 | C29—C30 | 1.522 (3) |
O11—C12 | 1.418 (2) | C29—H29A | 0.9900 |
C12—C13 | 1.499 (3) | C29—H29B | 0.9900 |
C12—H12A | 0.9900 | C30—C31 | 1.531 (3) |
C12—H12B | 0.9900 | C30—H30A | 0.9900 |
C13—O14 | 1.437 (2) | C30—H30B | 0.9900 |
C13—H13A | 0.9900 | C31—H31A | 0.9800 |
C13—H13B | 0.9900 | C31—H31B | 0.9800 |
O14—C15 | 1.369 (2) | C31—H31C | 0.9800 |
C15—C16 | 1.392 (3) | O32—C32 | 1.310 (2) |
C15—C20 | 1.402 (3) | O32—H32 | 0.9300 |
C16—C17 | 1.392 (3) | O33—C32 | 1.217 (3) |
C16—H16 | 0.9500 | C32—C33 | 1.502 (3) |
C17—C18 | 1.383 (3) | C33—H33A | 0.9800 |
C17—H17 | 0.9500 | C33—H33B | 0.9800 |
C18—C19 | 1.392 (3) | C33—H33C | 0.9800 |
C18—H18 | 0.9500 | ||
N25—C1—C2 | 111.06 (14) | C15—C20—C21 | 121.60 (15) |
N25—C1—C24 | 112.37 (13) | N25—C21—C20 | 111.21 (14) |
C2—C1—C24 | 112.90 (14) | N25—C21—C22 | 111.78 (13) |
N25—C1—H1 | 106.7 | C20—C21—C22 | 113.66 (14) |
C2—C1—H1 | 106.7 | N25—C21—H21 | 106.6 |
C24—C1—H1 | 106.7 | C20—C21—H21 | 106.6 |
C3—C2—C7 | 118.35 (16) | C22—C21—H21 | 106.6 |
C3—C2—C1 | 120.22 (16) | C23—C22—C26 | 105.47 (14) |
C7—C2—C1 | 121.42 (15) | C23—C22—C21 | 110.33 (14) |
C2—C3—C4 | 121.25 (17) | C26—C22—C21 | 109.81 (14) |
C2—C3—H3 | 119.4 | C23—C22—H22 | 110.4 |
C4—C3—H3 | 119.4 | C26—C22—H22 | 110.4 |
C5—C4—C3 | 119.51 (17) | C21—C22—H22 | 110.4 |
C5—C4—H4 | 120.2 | O23—C23—C24 | 124.69 (16) |
C3—C4—H4 | 120.2 | O23—C23—C22 | 124.22 (17) |
C4—C5—C6 | 120.77 (16) | C24—C23—C22 | 110.82 (15) |
C4—C5—H5 | 119.6 | C23—C24—C28 | 105.96 (14) |
C6—C5—H5 | 119.6 | C23—C24—C1 | 109.72 (14) |
C5—C6—C7 | 119.24 (17) | C28—C24—C1 | 111.30 (14) |
C5—C6—H6 | 120.4 | C23—C24—H24 | 109.9 |
C7—C6—H6 | 120.4 | C28—C24—H24 | 109.9 |
O8—C7—C6 | 124.44 (16) | C1—C24—H24 | 109.9 |
O8—C7—C2 | 114.69 (15) | C21—N25—C1 | 109.49 (13) |
C6—C7—C2 | 120.87 (16) | C21—N25—H25 | 108.3 |
C7—O8—C9 | 117.94 (14) | C1—N25—H25 | 109.1 |
O8—C9—C10 | 106.49 (14) | N27—C26—C22 | 110.50 (14) |
O8—C9—H9A | 110.4 | N27—C26—H26A | 109.6 |
C10—C9—H9A | 110.4 | C22—C26—H26A | 109.6 |
O8—C9—H9B | 110.4 | N27—C26—H26B | 109.6 |
C10—C9—H9B | 110.4 | C22—C26—H26B | 109.6 |
H9A—C9—H9B | 108.6 | H26A—C26—H26B | 108.1 |
O11—C10—C9 | 108.52 (15) | C26—N27—C28 | 111.21 (14) |
O11—C10—H10A | 110.0 | C26—N27—C29 | 110.59 (14) |
C9—C10—H10A | 110.0 | C28—N27—C29 | 113.43 (14) |
O11—C10—H10B | 110.0 | N27—C28—C24 | 110.26 (14) |
C9—C10—H10B | 110.0 | N27—C28—H28A | 109.6 |
H10A—C10—H10B | 108.4 | C24—C28—H28A | 109.6 |
C12—O11—C10 | 114.24 (15) | N27—C28—H28B | 109.6 |
O11—C12—C13 | 108.19 (15) | C24—C28—H28B | 109.6 |
O11—C12—H12A | 110.1 | H28A—C28—H28B | 108.1 |
C13—C12—H12A | 110.1 | N27—C29—C30 | 114.01 (15) |
O11—C12—H12B | 110.1 | N27—C29—H29A | 108.7 |
C13—C12—H12B | 110.1 | C30—C29—H29A | 108.7 |
H12A—C12—H12B | 108.4 | N27—C29—H29B | 108.7 |
O14—C13—C12 | 106.24 (15) | C30—C29—H29B | 108.7 |
O14—C13—H13A | 110.5 | H29A—C29—H29B | 107.6 |
C12—C13—H13A | 110.5 | C29—C30—C31 | 110.60 (17) |
O14—C13—H13B | 110.5 | C29—C30—H30A | 109.5 |
C12—C13—H13B | 110.5 | C31—C30—H30A | 109.5 |
H13A—C13—H13B | 108.7 | C29—C30—H30B | 109.5 |
C15—O14—C13 | 118.86 (14) | C31—C30—H30B | 109.5 |
O14—C15—C16 | 124.32 (17) | H30A—C30—H30B | 108.1 |
O14—C15—C20 | 114.57 (15) | C30—C31—H31A | 109.5 |
C16—C15—C20 | 121.10 (17) | C30—C31—H31B | 109.5 |
C15—C16—C17 | 118.93 (18) | H31A—C31—H31B | 109.5 |
C15—C16—H16 | 120.5 | C30—C31—H31C | 109.5 |
C17—C16—H16 | 120.5 | H31A—C31—H31C | 109.5 |
C18—C17—C16 | 121.24 (18) | H31B—C31—H31C | 109.5 |
C18—C17—H17 | 119.4 | C32—O32—H32 | 111.9 |
C16—C17—H17 | 119.4 | O33—C32—O32 | 124.0 (2) |
C17—C18—C19 | 119.05 (19) | O33—C32—C33 | 122.7 (2) |
C17—C18—H18 | 120.5 | O32—C32—C33 | 113.3 (2) |
C19—C18—H18 | 120.5 | C32—C33—H33A | 109.5 |
C18—C19—C20 | 121.43 (18) | C32—C33—H33B | 109.5 |
C18—C19—H19 | 119.3 | H33A—C33—H33B | 109.5 |
C20—C19—H19 | 119.3 | C32—C33—H33C | 109.5 |
C19—C20—C15 | 118.25 (16) | H33A—C33—H33C | 109.5 |
C19—C20—C21 | 120.15 (16) | H33B—C33—H33C | 109.5 |
N25—C1—C2—C3 | −120.84 (17) | C19—C20—C21—N25 | 111.18 (17) |
C24—C1—C2—C3 | 111.90 (18) | C15—C20—C21—N25 | −68.4 (2) |
N25—C1—C2—C7 | 60.4 (2) | C19—C20—C21—C22 | −121.62 (17) |
C24—C1—C2—C7 | −66.9 (2) | C15—C20—C21—C22 | 58.8 (2) |
C7—C2—C3—C4 | 0.4 (3) | N25—C21—C22—C23 | −2.93 (19) |
C1—C2—C3—C4 | −178.42 (17) | C20—C21—C22—C23 | −129.83 (15) |
C2—C3—C4—C5 | −1.1 (3) | N25—C21—C22—C26 | −118.76 (15) |
C3—C4—C5—C6 | 0.5 (3) | C20—C21—C22—C26 | 114.33 (16) |
C4—C5—C6—C7 | 0.8 (3) | C26—C22—C23—O23 | −110.80 (19) |
C5—C6—C7—O8 | 178.32 (17) | C21—C22—C23—O23 | 130.67 (18) |
C5—C6—C7—C2 | −1.5 (3) | C26—C22—C23—C24 | 63.50 (17) |
C3—C2—C7—O8 | −178.95 (15) | C21—C22—C23—C24 | −55.02 (18) |
C1—C2—C7—O8 | −0.1 (2) | O23—C23—C24—C28 | 111.02 (19) |
C3—C2—C7—C6 | 0.9 (3) | C22—C23—C24—C28 | −63.25 (17) |
C1—C2—C7—C6 | 179.71 (16) | O23—C23—C24—C1 | −128.72 (18) |
C6—C7—O8—C9 | 0.1 (2) | C22—C23—C24—C1 | 57.00 (18) |
C2—C7—O8—C9 | 179.88 (15) | N25—C1—C24—C23 | −1.16 (19) |
C7—O8—C9—C10 | −175.18 (15) | C2—C1—C24—C23 | 125.40 (16) |
O8—C9—C10—O11 | −69.33 (18) | N25—C1—C24—C28 | 115.80 (15) |
C9—C10—O11—C12 | 157.26 (15) | C2—C1—C24—C28 | −117.65 (16) |
C10—O11—C12—C13 | −156.70 (15) | C20—C21—N25—C1 | −173.72 (14) |
O11—C12—C13—O14 | 65.88 (19) | C22—C21—N25—C1 | 58.06 (17) |
C12—C13—O14—C15 | −173.95 (15) | C2—C1—N25—C21 | 176.47 (13) |
C13—O14—C15—C16 | 0.5 (3) | C24—C1—N25—C21 | −55.99 (17) |
C13—O14—C15—C20 | 179.35 (15) | C23—C22—C26—N27 | −60.27 (18) |
O14—C15—C16—C17 | 178.54 (17) | C21—C22—C26—N27 | 58.60 (18) |
C20—C15—C16—C17 | −0.2 (3) | C22—C26—N27—C28 | 60.27 (18) |
C15—C16—C17—C18 | 0.6 (3) | C22—C26—N27—C29 | −172.75 (14) |
C16—C17—C18—C19 | −0.5 (3) | C26—N27—C28—C24 | −59.54 (18) |
C17—C18—C19—C20 | 0.0 (3) | C29—N27—C28—C24 | 175.04 (14) |
C18—C19—C20—C15 | 0.4 (3) | C23—C24—C28—N27 | 59.27 (18) |
C18—C19—C20—C21 | −179.16 (17) | C1—C24—C28—N27 | −59.95 (18) |
O14—C15—C20—C19 | −179.19 (15) | C26—N27—C29—C30 | 169.32 (15) |
C16—C15—C20—C19 | −0.3 (3) | C28—N27—C29—C30 | −64.9 (2) |
O14—C15—C20—C21 | 0.4 (2) | N27—C29—C30—C31 | −161.57 (16) |
C16—C15—C20—C21 | 179.25 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N25—H25···O8 | 0.91 | 2.27 | 2.867 (2) | 123 |
N25—H25···O14 | 0.91 | 2.45 | 3.008 (2) | 120 |
O32—H32···N25 | 0.93 | 1.67 | 2.595 (2) | 176 |
C1—H1···O33 | 1.00 | 2.57 | 3.249 (3) | 125 |
C5—H5···O32i | 0.95 | 2.58 | 3.442 (2) | 152 |
C16—H16···O32ii | 0.95 | 2.47 | 3.340 (2) | 153 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, −y+1, −z. |
Acknowledgements
This research was funded by the Vietnam National Foundation for Science and Technology Development (NAFOSTED) under grant number 104.01–2014.39.
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