24-Acetyl-8,11,14-trioxa-24,27-diaza­penta­cyclo­[19.5.1.122,26.02,7.015,20]octa­cosa-2,4,6,15(20),16,18-hexaen-28-one

Anh, L.T.; Hieu, T.H.; Soldatenkov, A.T.; Kolyadina, N.M.; Khrustalev, V.N.

doi:10.1107/S1600536812027274

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Pages o2165-o2166

https://doi.org/10.1107/S1600536812027274

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24-Acetyl-8,11,14-trioxa-24,27-diazapentacyclo[19.5.1.1^22,26.0^2,7.0^15,20]octacosa-2,4,6,15(20),16,18-hexaen-28-one

Le Tuan Anh,^a ^* Truong Hong Hieu,^a Anatoly T. Soldatenkov,^b Nadezhda M. Kolyadina ^b and Victor N. Khrustalev ^c

^aDepartment of Chemistry, Vietnam National University, 144 Xuan Thuy, Cau Giay, Hanoi, Vietnam, ^bOrganic Chemistry Department, Russian Peoples Friendship University, Miklukho-Maklaya St 6, Moscow, 117198, Russia, and ^cX-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: vkh@xray.ineos.ac.ru

(Received 13 June 2012; accepted 15 June 2012; online 23 June 2012)

The title compound, C₂₅H₂₈N₂O₅, is a product of the Petrenko–Kritchenko condensation of N-acetylpiperidone with 1,5-bis(2-formylphenoxy)-3-oxapentane and ammonium acetate. The molecule comprises a fused pentacyclic system containing an aza-14-crown-3-ether macrocycle, two piperidone and two benzene rings. The aza-14-crown-3-ether ring adopts a bowl conformation. The dihedral angle between the benzene rings fused to the aza-14-crown-4-ether unit is 70.18 (4)°. The central piperidone ring has a boat conformation, whereas the terminal piperidone ring adopts a chair conformation. The conformation of the central piperidone ring is determined by two intramolecular N—H⋯O hydrogen bonds. In the crystal, molecules are linked by weak C—H⋯O interactions into chains along [010].

Related literature

For general background to the design, synthesis and applications of macrocyclic ligands for coordination and supramolecular chemistry, see: Hiraoka (1978 ); Pedersen (1988 ); Gokel & Murillo (1996 ); Bradshaw & Izatt (1997 ). For related compounds, see: Levov et al. (2006 , 2008 ); Komarova et al. (2008 ); Anh et al. (2008 , 2012a ,b ); Hieu et al. (2011 ); Khieu et al. (2011 ); Sokol et al. (2011 ).

Experimental

Crystal data

C₂₅H₂₈N₂O₅
M_r = 436.49
Orthorhombic, P b c a
a = 17.1756 (6) Å
b = 11.1724 (4) Å
c = 22.6546 (8) Å
V = 4347.3 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.973, T_max = 0.977
54466 measured reflections
6326 independent reflections
4682 reflections with I > 2σ(I)
R_int = 0.069

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.106
S = 1.00
6326 reflections
293 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N27—H27⋯O8	0.90 (2)	2.49 (2)	3.0337 (13)	119 (1)
N27—H27⋯O14	0.90 (2)	2.44 (1)	3.0193 (13)	122 (1)
C21—H21⋯O28ⁱ	1.00	2.48	3.4683 (14)	168
C30—H30B⋯O28ⁱ	0.98	2.51	3.0556 (16)	115
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2001 ); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812027274/aa2068sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812027274/aa2068Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812027274/aa2068Isup3.cml

checkCIF report

Comment top

Design, synthesis and applications of macrocyclic ligands for coordination and supramolecular chemistry draw very great attention of investigators during the last several decades (Hiraoka, 1978; Pedersen, 1988; Gokel & Murillo, 1996; Bradshaw & Izatt, 1997). Recently we have developed the effective methods of synthesis of azacrown ethers containing piperidine (Levov et al., 2006, 2008; Anh et al., 2008, 2012a, 2012b), 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 for obtaining of a macrocyclic ligand containing N-acylsubstituted bispidine moiety, we studied the Petrenko-Kritchenko condensation of the N-acetylpiperidone with 1,5-bis(2-formylphenoxy)-3-oxapentane and ammonium acetate. The reaction have proceeded smoothly to give the expected azacrown system with a good yield (Fig. 1).

The molecule of the title compound, C₂₅H₂₈ N₂O₅, comprises a fused pentacyclic system containing the aza-14-crown-3-ether macrocycle, two piperidone and two benzene rings (Fig. 2). The aza-14-crown-3-ether ring adopts a bowl conformation. The configuration 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 70.18 (4)°. The central piperidone ring has a boat conformation, whereas the terminal piperidone ring adopts a chair conformation. Apparently, the conformation of the central piperidone ring is determined by the two intramolecular N–H···O hydrogen bonds (Table 1). The nitrogen N24 atom has a trigonal-planar geometry (sum of the bond angles is 359.8°), while the nitrogen N27 atom adopts a trigonal-pyramidal geometry (sum of the bond angles is 326.7°).

The molecule of the title compound possesses four asymmetric centers at the C1, C21, C22 and C26 carbon atoms and can have potentially numerous diastereomers. The crystal of the title compound is racemic and consists of enantiomeric pairs with the following relative configuration of the centers: rac-1R*, 21S*,22R*,26S*.

In the crystal, the molecules are bound by the weak intermolecular C–H···O hydrogen bonding interactions into the chains along [010] (Fig. 3, Table 1). The crystal packing of the chains is stacking along the a axis (Fig. 3).

Related literature top

For general background to the design, synthesis and applications of macrocyclic ligands for coordination and supramolecular chemistry, see: Hiraoka (1978); Pedersen (1988); Gokel & Murillo (1996); Bradshaw & Izatt (1997). For related compounds, see: Levov et al. (2006, 2008); Komarova et al. (2008); Anh et al. (2008, 2012a,b); Hieu et al. (2011); Khieu et al. (2011); Sokol et al. (2011).

Experimental top

Ammonium acetate (3.0 g, 39.0 mmol) was added to a solution of 1,5-bis(2-formylphenoxy)-3-oxapentane (3.14 g, 10.0 mmol) and N-acetylpiperidone (1.41 g, 10.0 mmol) in ethanol-acetic acid mixture (30 ml 1 ml). The reaction mixture was stirred at 293 K for 3 days (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 re-crystallized from ethanol to give 2.54 g of white crystals of the title compound. Yield is 58%. M.p.= 500–502 K. IR (KBr), ν/cm^-1: 1603, 1649, 1713, 3405, 3460. ¹H NMR (CDCl₃, 400 MHz, 300 K): δ = 2.37 (s, 3H, CH₃C=O), 2.91 (m, 3H, H22, H26 and H27), 3.47 and 4.98 (both dd, 1H each, H1 and H21, J = 7.3 and 1.1), 3.92–4.10 (m, 12H, OCH₂CH₂OCH₂CH₂O, 2H23 and 2H25), 6.75–6.95 (m, 3H, H_arom), 7.21–7.36 (m, 5H, H_arom). Anal. Calcd. for C₂₅H₂₈N₂O₅: C, 68.79; H, 6.47; N, 6.42. Found: C, 69.03; H, 6.52; N, 6.43.

Structure description top

For general background to the design, synthesis and applications of macrocyclic ligands for coordination and supramolecular chemistry, see: Hiraoka (1978); Pedersen (1988); Gokel & Murillo (1996); Bradshaw & Izatt (1997). For related compounds, see: Levov et al. (2006, 2008); Komarova et al. (2008); Anh et al. (2008, 2012a,b); Hieu et al. (2011); Khieu et al. (2011); Sokol et al. (2011).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: 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).

Figures top

	Fig. 1. Petrenko-Kritchenko condensation of the N-acetylpiperidone with 1,5-bis(2-formylphenoxy)-3-oxapentane and ammonium acetate.
	Fig. 2. Molecular structure of I. Displacement ellipsoids are shown at the 50% probability level. H atoms are presented as small spheres of arbitrary radius. Dashed lines indicate the intramolecular N–H···O hydrogen bonds.
	Fig. 3. The H-bonded chains of I along the b axis. Dashed lines indicate the intramolecular N–H···O and intermolecular C–H···O hydrogen bonds.

24-Acetyl-8,11,14-trioxa-24,27- diazapentacyclo[19.5.1.1^22,26.0^2,7.0^15,20]octacosa- 2,4,6,15(20),16,18-hexaen-28-one top

Crystal data top

C₂₅H₂₈N₂O₅	F(000) = 1856
M_r = 436.49	D_x = 1.334 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6757 reflections
a = 17.1756 (6) Å	θ = 2.4–27.6°
b = 11.1724 (4) Å	µ = 0.09 mm⁻¹
c = 22.6546 (8) Å	T = 100 K
V = 4347.3 (3) Å³	Prism, colourless
Z = 8	0.30 × 0.25 × 0.25 mm

Data collection top

Bruker APEXII CCD diffractometer	6326 independent reflections
Radiation source: fine-focus sealed tube	4682 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
φ and ω scans	θ_max = 30.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −24→24
T_min = 0.973, T_max = 0.977	k = −15→15
54466 measured reflections	l = −31→31

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: mixed
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0483P)² + 1.18P] where P = (F_o² + 2F_c²)/3
6326 reflections	(Δ/σ)_max < 0.001
293 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₅H₂₈N₂O₅	V = 4347.3 (3) Å³
M_r = 436.49	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 17.1756 (6) Å	µ = 0.09 mm⁻¹
b = 11.1724 (4) Å	T = 100 K
c = 22.6546 (8) Å	0.30 × 0.25 × 0.25 mm

Data collection top

Bruker APEXII CCD diffractometer	6326 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	4682 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.977	R_int = 0.069
54466 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.34 e Å⁻³
6326 reflections	Δρ_min = −0.24 e Å⁻³
293 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.14643 (7)	0.45850 (10)	0.11628 (5)	0.0150 (2)
H1	0.1927	0.4136	0.1012	0.018*
C2	0.07641 (7)	0.40656 (10)	0.08499 (5)	0.0176 (2)
C3	0.08519 (8)	0.30961 (11)	0.04720 (6)	0.0242 (3)
H3	0.1359	0.2793	0.0398	0.029*
C4	0.02150 (9)	0.25559 (12)	0.01993 (6)	0.0302 (3)
H4	0.0288	0.1886	−0.0053	0.036*
C5	−0.05235 (8)	0.30019 (12)	0.02980 (6)	0.0276 (3)
H5	−0.0960	0.2627	0.0120	0.033*
C6	−0.06308 (8)	0.39996 (12)	0.06580 (6)	0.0238 (3)
H6	−0.1137	0.4321	0.0715	0.029*
C7	0.00101 (7)	0.45237 (11)	0.09343 (5)	0.0194 (2)
O8	−0.00310 (5)	0.54876 (8)	0.13029 (4)	0.0238 (2)
C9	−0.07793 (7)	0.59780 (13)	0.14482 (6)	0.0262 (3)
H9A	−0.1115	0.5361	0.1632	0.031*
H9B	−0.1042	0.6285	0.1090	0.031*
C10	−0.06217 (8)	0.69751 (13)	0.18737 (6)	0.0273 (3)
H10A	−0.0258	0.7561	0.1696	0.033*
H10B	−0.1112	0.7394	0.1973	0.033*
O11	−0.02887 (5)	0.64651 (8)	0.23893 (4)	0.0245 (2)
C12	0.01097 (7)	0.73098 (12)	0.27487 (6)	0.0244 (3)
H12A	−0.0268	0.7808	0.2968	0.029*
H12B	0.0435	0.7842	0.2501	0.029*
C13	0.06106 (7)	0.66211 (12)	0.31701 (6)	0.0235 (3)
H13A	0.0838	0.7167	0.3468	0.028*
H13B	0.0296	0.6010	0.3378	0.028*
O14	0.12189 (5)	0.60544 (8)	0.28352 (4)	0.01997 (18)
C15	0.16485 (7)	0.51843 (11)	0.31095 (5)	0.0174 (2)
C16	0.16080 (7)	0.49369 (12)	0.37114 (5)	0.0222 (3)
H16	0.1278	0.5396	0.3960	0.027*
C17	0.20549 (8)	0.40101 (12)	0.39451 (6)	0.0241 (3)
H17	0.2017	0.3825	0.4353	0.029*
C18	0.25533 (7)	0.33568 (12)	0.35910 (6)	0.0220 (3)
H18	0.2856	0.2725	0.3753	0.026*
C19	0.26073 (7)	0.36366 (11)	0.29901 (5)	0.0178 (2)
H19	0.2962	0.3205	0.2749	0.021*
C20	0.21530 (6)	0.45337 (10)	0.27385 (5)	0.0149 (2)
C21	0.21819 (6)	0.47517 (10)	0.20788 (5)	0.0139 (2)
H21	0.2596	0.4215	0.1917	0.017*
C22	0.24208 (6)	0.60694 (10)	0.19154 (5)	0.0144 (2)
H22	0.2505	0.6539	0.2286	0.017*
C23	0.31604 (7)	0.61447 (11)	0.15252 (5)	0.0174 (2)
H23A	0.3315	0.6993	0.1480	0.021*
H23B	0.3593	0.5717	0.1723	0.021*
N24	0.30278 (6)	0.56178 (9)	0.09399 (4)	0.0182 (2)
C25	0.23402 (7)	0.60548 (11)	0.06232 (5)	0.0194 (2)
H25A	0.2272	0.5590	0.0255	0.023*
H25B	0.2417	0.6905	0.0515	0.023*
C26	0.16073 (7)	0.59325 (10)	0.10078 (5)	0.0160 (2)
H26	0.1145	0.6273	0.0798	0.019*
N27	0.14364 (6)	0.43716 (9)	0.18055 (4)	0.01508 (19)
H27	0.1049 (9)	0.4816 (13)	0.1957 (6)	0.018*
C28	0.17742 (7)	0.66361 (10)	0.15626 (5)	0.0159 (2)
O28	0.14686 (5)	0.75881 (8)	0.16807 (4)	0.02178 (19)
C29	0.35168 (7)	0.48363 (12)	0.06601 (6)	0.0224 (3)
O29	0.33441 (7)	0.43974 (10)	0.01789 (4)	0.0370 (3)
C30	0.42915 (7)	0.45517 (12)	0.09395 (6)	0.0250 (3)
H30A	0.4494	0.3803	0.0774	0.037*
H30B	0.4225	0.4464	0.1367	0.037*
H30C	0.4659	0.5203	0.0859	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0160 (5)	0.0145 (5)	0.0144 (5)	0.0005 (4)	−0.0013 (4)	−0.0007 (4)
C2	0.0214 (6)	0.0161 (5)	0.0153 (5)	−0.0028 (4)	−0.0044 (4)	0.0024 (4)
C3	0.0305 (7)	0.0199 (6)	0.0223 (6)	0.0040 (5)	−0.0115 (5)	−0.0018 (5)
C4	0.0432 (8)	0.0197 (6)	0.0276 (7)	0.0000 (6)	−0.0188 (6)	−0.0032 (5)
C5	0.0351 (7)	0.0251 (7)	0.0225 (6)	−0.0113 (6)	−0.0147 (6)	0.0067 (5)
C6	0.0200 (6)	0.0304 (7)	0.0212 (6)	−0.0071 (5)	−0.0041 (5)	0.0069 (5)
C7	0.0207 (6)	0.0207 (6)	0.0167 (5)	−0.0047 (5)	−0.0024 (4)	0.0033 (4)
O8	0.0147 (4)	0.0290 (5)	0.0278 (5)	−0.0003 (3)	0.0011 (3)	−0.0074 (4)
C9	0.0138 (5)	0.0349 (7)	0.0298 (7)	0.0033 (5)	0.0000 (5)	0.0000 (6)
C10	0.0203 (6)	0.0303 (7)	0.0312 (7)	0.0083 (5)	−0.0001 (5)	0.0006 (6)
O11	0.0229 (4)	0.0251 (5)	0.0254 (5)	0.0009 (4)	−0.0005 (4)	−0.0010 (4)
C12	0.0203 (6)	0.0234 (6)	0.0296 (7)	0.0037 (5)	0.0038 (5)	−0.0072 (5)
C13	0.0199 (6)	0.0281 (7)	0.0225 (6)	0.0034 (5)	0.0066 (5)	−0.0068 (5)
O14	0.0195 (4)	0.0211 (4)	0.0193 (4)	0.0053 (3)	0.0051 (3)	−0.0004 (3)
C15	0.0157 (5)	0.0191 (5)	0.0174 (5)	−0.0020 (4)	0.0000 (4)	−0.0015 (4)
C16	0.0217 (6)	0.0274 (6)	0.0173 (6)	−0.0020 (5)	0.0013 (5)	−0.0024 (5)
C17	0.0249 (6)	0.0326 (7)	0.0148 (5)	−0.0066 (5)	−0.0036 (5)	0.0025 (5)
C18	0.0214 (6)	0.0239 (6)	0.0206 (6)	−0.0034 (5)	−0.0072 (5)	0.0030 (5)
C19	0.0169 (5)	0.0180 (5)	0.0187 (5)	−0.0025 (4)	−0.0029 (4)	−0.0023 (4)
C20	0.0147 (5)	0.0153 (5)	0.0146 (5)	−0.0034 (4)	−0.0014 (4)	−0.0018 (4)
C21	0.0137 (5)	0.0138 (5)	0.0142 (5)	−0.0004 (4)	−0.0005 (4)	−0.0015 (4)
C22	0.0145 (5)	0.0132 (5)	0.0156 (5)	−0.0009 (4)	0.0018 (4)	−0.0028 (4)
C23	0.0153 (5)	0.0187 (5)	0.0182 (5)	−0.0020 (4)	0.0027 (4)	−0.0024 (4)
N24	0.0160 (5)	0.0218 (5)	0.0167 (5)	−0.0009 (4)	0.0027 (4)	−0.0018 (4)
C25	0.0184 (5)	0.0232 (6)	0.0166 (5)	−0.0019 (5)	0.0017 (4)	0.0027 (5)
C26	0.0162 (5)	0.0152 (5)	0.0165 (5)	−0.0007 (4)	0.0006 (4)	0.0024 (4)
N27	0.0154 (4)	0.0157 (5)	0.0141 (4)	−0.0021 (4)	−0.0012 (4)	−0.0002 (3)
C28	0.0143 (5)	0.0145 (5)	0.0190 (5)	−0.0026 (4)	0.0037 (4)	0.0019 (4)
O28	0.0217 (4)	0.0150 (4)	0.0286 (5)	0.0028 (3)	0.0010 (4)	−0.0012 (3)
C29	0.0234 (6)	0.0222 (6)	0.0215 (6)	0.0003 (5)	0.0039 (5)	−0.0020 (5)
O29	0.0422 (6)	0.0448 (6)	0.0238 (5)	0.0150 (5)	−0.0044 (4)	−0.0134 (4)
C30	0.0200 (6)	0.0283 (7)	0.0266 (6)	0.0009 (5)	0.0044 (5)	−0.0053 (5)

Geometric parameters (Å, º) top

C1—N27	1.4761 (14)	C16—C17	1.3936 (19)
C1—C2	1.5118 (16)	C16—H16	0.9500
C1—C26	1.5653 (16)	C17—C18	1.3816 (19)
C1—H1	1.0000	C17—H17	0.9500
C2—C3	1.3888 (17)	C18—C19	1.3999 (17)
C2—C7	1.4056 (17)	C18—H18	0.9500
C3—C4	1.3937 (18)	C19—C20	1.3923 (16)
C3—H3	0.9500	C19—H19	0.9500
C4—C5	1.381 (2)	C20—C21	1.5151 (15)
C4—H4	0.9500	C21—N27	1.4843 (14)
C5—C6	1.394 (2)	C21—C22	1.5725 (16)
C5—H5	0.9500	C21—H21	1.0000
C6—C7	1.3950 (17)	C22—C28	1.5076 (16)
C6—H6	0.9500	C22—C23	1.5497 (15)
C7—O8	1.3646 (15)	C22—H22	1.0000
O8—C9	1.4353 (15)	C23—N24	1.4686 (15)
C9—C10	1.498 (2)	C23—H23A	0.9900
C9—H9A	0.9900	C23—H23B	0.9900
C9—H9B	0.9900	N24—C29	1.3674 (16)
C10—O11	1.4199 (16)	N24—C25	1.4655 (15)
C10—H10A	0.9900	C25—C26	1.5370 (16)
C10—H10B	0.9900	C25—H25A	0.9900
O11—C12	1.4220 (16)	C25—H25B	0.9900
C12—C13	1.4978 (19)	C26—C28	1.5099 (16)
C12—H12A	0.9900	C26—H26	1.0000
C12—H12B	0.9900	N27—H27	0.898 (15)
C13—O14	1.4381 (14)	C28—O28	1.2159 (14)
C13—H13A	0.9900	C29—O29	1.2314 (16)
C13—H13B	0.9900	C29—C30	1.5074 (18)
O14—C15	1.3694 (14)	C30—H30A	0.9800
C15—C16	1.3930 (16)	C30—H30B	0.9800
C15—C20	1.4091 (16)	C30—H30C	0.9800

N27—C1—C2	112.01 (9)	C16—C17—H17	119.6
N27—C1—C26	112.44 (9)	C17—C18—C19	119.19 (12)
C2—C1—C26	112.88 (9)	C17—C18—H18	120.4
N27—C1—H1	106.3	C19—C18—H18	120.4
C2—C1—H1	106.3	C20—C19—C18	121.45 (11)
C26—C1—H1	106.3	C20—C19—H19	119.3
C3—C2—C7	117.89 (11)	C18—C19—H19	119.3
C3—C2—C1	120.13 (11)	C19—C20—C15	118.16 (10)
C7—C2—C1	121.96 (10)	C19—C20—C21	120.07 (10)
C2—C3—C4	121.72 (13)	C15—C20—C21	121.71 (10)
C2—C3—H3	119.1	N27—C21—C20	109.71 (9)
C4—C3—H3	119.1	N27—C21—C22	113.25 (9)
C5—C4—C3	119.53 (13)	C20—C21—C22	113.03 (9)
C5—C4—H4	120.2	N27—C21—H21	106.8
C3—C4—H4	120.2	C20—C21—H21	106.8
C4—C5—C6	120.32 (12)	C22—C21—H21	106.8
C4—C5—H5	119.8	C28—C22—C23	106.18 (9)
C6—C5—H5	119.8	C28—C22—C21	109.01 (9)
C5—C6—C7	119.60 (13)	C23—C22—C21	113.51 (9)
C5—C6—H6	120.2	C28—C22—H22	109.3
C7—C6—H6	120.2	C23—C22—H22	109.3
O8—C7—C6	124.40 (12)	C21—C22—H22	109.3
O8—C7—C2	114.73 (10)	N24—C23—C22	111.47 (9)
C6—C7—C2	120.87 (12)	N24—C23—H23A	109.3
C7—O8—C9	119.20 (10)	C22—C23—H23A	109.3
O8—C9—C10	105.64 (10)	N24—C23—H23B	109.3
O8—C9—H9A	110.6	C22—C23—H23B	109.3
C10—C9—H9A	110.6	H23A—C23—H23B	108.0
O8—C9—H9B	110.6	C29—N24—C25	118.73 (10)
C10—C9—H9B	110.6	C29—N24—C23	125.40 (10)
H9A—C9—H9B	108.7	C25—N24—C23	115.69 (9)
O11—C10—C9	107.69 (11)	N24—C25—C26	110.66 (9)
O11—C10—H10A	110.2	N24—C25—H25A	109.5
C9—C10—H10A	110.2	C26—C25—H25A	109.5
O11—C10—H10B	110.2	N24—C25—H25B	109.5
C9—C10—H10B	110.2	C26—C25—H25B	109.5
H10A—C10—H10B	108.5	H25A—C25—H25B	108.1
C10—O11—C12	113.49 (10)	C28—C26—C25	105.67 (9)
O11—C12—C13	107.48 (11)	C28—C26—C1	110.10 (9)
O11—C12—H12A	110.2	C25—C26—C1	109.95 (9)
C13—C12—H12A	110.2	C28—C26—H26	110.3
O11—C12—H12B	110.2	C25—C26—H26	110.3
C13—C12—H12B	110.2	C1—C26—H26	110.3
H12A—C12—H12B	108.5	C1—N27—C21	109.71 (9)
O14—C13—C12	107.90 (10)	C1—N27—H27	108.2 (9)
O14—C13—H13A	110.1	C21—N27—H27	108.8 (9)
C12—C13—H13A	110.1	O28—C28—C22	124.66 (11)
O14—C13—H13B	110.1	O28—C28—C26	123.82 (11)
C12—C13—H13B	110.1	C22—C28—C26	111.26 (9)
H13A—C13—H13B	108.4	O29—C29—N24	121.11 (12)
C15—O14—C13	117.69 (9)	O29—C29—C30	120.02 (12)
O14—C15—C16	123.92 (11)	N24—C29—C30	118.83 (11)
O14—C15—C20	115.27 (10)	C29—C30—H30A	109.5
C16—C15—C20	120.81 (11)	C29—C30—H30B	109.5
C15—C16—C17	119.46 (12)	H30A—C30—H30B	109.5
C15—C16—H16	120.3	C29—C30—H30C	109.5
C17—C16—H16	120.3	H30A—C30—H30C	109.5
C18—C17—C16	120.88 (12)	H30B—C30—H30C	109.5
C18—C17—H17	119.6

N27—C1—C2—C3	−111.77 (12)	C19—C20—C21—N27	110.05 (11)
C26—C1—C2—C3	120.11 (12)	C15—C20—C21—N27	−67.13 (13)
N27—C1—C2—C7	67.29 (14)	C19—C20—C21—C22	−122.51 (11)
C26—C1—C2—C7	−60.83 (14)	C15—C20—C21—C22	60.31 (14)
C7—C2—C3—C4	−2.39 (19)	N27—C21—C22—C28	5.27 (12)
C1—C2—C3—C4	176.71 (12)	C20—C21—C22—C28	−120.29 (10)
C2—C3—C4—C5	1.0 (2)	N27—C21—C22—C23	−112.85 (10)
C3—C4—C5—C6	1.3 (2)	C20—C21—C22—C23	121.59 (10)
C4—C5—C6—C7	−2.06 (19)	C28—C22—C23—N24	−53.90 (12)
C5—C6—C7—O8	−178.82 (11)	C21—C22—C23—N24	65.84 (12)
C5—C6—C7—C2	0.61 (18)	C22—C23—N24—C29	−133.39 (12)
C3—C2—C7—O8	−178.95 (11)	C22—C23—N24—C25	51.51 (13)
C1—C2—C7—O8	1.97 (16)	C29—N24—C25—C26	131.12 (11)
C3—C2—C7—C6	1.57 (18)	C23—N24—C25—C26	−53.45 (13)
C1—C2—C7—C6	−177.51 (11)	N24—C25—C26—C28	57.62 (12)
C6—C7—O8—C9	3.31 (18)	N24—C25—C26—C1	−61.17 (12)
C2—C7—O8—C9	−176.15 (11)	N27—C1—C26—C28	6.70 (13)
C7—O8—C9—C10	177.69 (11)	C2—C1—C26—C28	134.60 (10)
O8—C9—C10—O11	−63.66 (13)	N27—C1—C26—C25	122.73 (10)
C9—C10—O11—C12	161.37 (10)	C2—C1—C26—C25	−109.37 (11)
C10—O11—C12—C13	−164.28 (10)	C2—C1—N27—C21	172.45 (9)
O11—C12—C13—O14	68.21 (13)	C26—C1—N27—C21	−59.19 (12)
C12—C13—O14—C15	−166.84 (10)	C20—C21—N27—C1	179.95 (9)
C13—O14—C15—C16	−9.56 (17)	C22—C21—N27—C1	52.63 (12)
C13—O14—C15—C20	170.68 (10)	C23—C22—C28—O28	−110.25 (12)
O14—C15—C16—C17	178.30 (11)	C21—C22—C28—O28	127.11 (12)
C20—C15—C16—C17	−1.95 (18)	C23—C22—C28—C26	64.03 (11)
C15—C16—C17—C18	1.83 (19)	C21—C22—C28—C26	−58.60 (11)
C16—C17—C18—C19	0.10 (19)	C25—C26—C28—O28	108.24 (12)
C17—C18—C19—C20	−1.97 (18)	C1—C26—C28—O28	−133.08 (11)
C18—C19—C20—C15	1.83 (17)	C25—C26—C28—C22	−66.11 (11)
C18—C19—C20—C21	−175.45 (10)	C1—C26—C28—C22	52.58 (12)
O14—C15—C20—C19	179.92 (10)	C25—N24—C29—O29	−8.16 (18)
C16—C15—C20—C19	0.15 (17)	C23—N24—C29—O29	176.88 (12)
O14—C15—C20—C21	−2.85 (16)	C25—N24—C29—C30	169.51 (11)
C16—C15—C20—C21	177.38 (11)	C23—N24—C29—C30	−5.45 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N27—H27···O8	0.90 (2)	2.49 (2)	3.0337 (13)	119 (1)
N27—H27···O14	0.90 (2)	2.44 (1)	3.0193 (13)	122 (1)
C21—H21···O28ⁱ	1.00	2.48	3.4683 (14)	168
C30—H30B···O28ⁱ	0.98	2.51	3.0556 (16)	115

Symmetry code: (i) −x+1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₈N₂O₅
M_r	436.49
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	17.1756 (6), 11.1724 (4), 22.6546 (8)
V (Å³)	4347.3 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.25 × 0.25

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.973, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	54466, 6326, 4682
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.106, 1.00
No. of reflections	6326
No. of parameters	293
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.24

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N27—H27···O8	0.90 (2)	2.49 (2)	3.0337 (13)	119 (1)
N27—H27···O14	0.90 (2)	2.44 (1)	3.0193 (13)	122 (1)
C21—H21···O28ⁱ	1.00	2.48	3.4683 (14)	168
C30—H30B···O28ⁱ	0.98	2.51	3.0556 (16)	115

Symmetry code: (i) −x+1/2, y−1/2, z.

Acknowledgements

We thank the Vietnam National University, Hanoi, (grant No. QG.11.09) for the financial support of this work.

References

Anh, L. T., Hieu, T. H., Soldatenkov, A. T., Kolyadina, N. M. & Khrustalev, V. N. (2012b). Acta Cryst. E68, o1588–o1589. CSD CrossRef IUCr Journals Google Scholar
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Volume 68| Part 7| July 2012| Pages o2165-o2166

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

24-Acetyl-8,11,14-trioxa-24,27-di­aza­penta­cyclo­[19.5.1.122,26.02,7.015,20]octa­cosa-2,4,6,15(20),16,18-hexaen-28-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

24-Acetyl-8,11,14-trioxa-24,27-diazapentacyclo[19.5.1.1^22,26.0^2,7.0^15,20]octacosa-2,4,6,15(20),16,18-hexaen-28-one