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Volume 69 
Part 4 
Pages o565-o566  
April 2013  

Received 13 March 2013
Accepted 16 March 2013
Online 23 March 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.094
Data-to-parameter ratio = 22.0
Details
Open access

Ethyl 23-benzyl-8,11,14-trioxa-23,28,29-triazapentacyclo[19.7.1.02,7.015,20.022,27]nonacosa-2,4,6,15(20),16,18,21,26-octaene-26-carboxylate

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: thh1101@yahoo.com

The title compound, C33H35N3O5, is the product of the multicomponent condensation of 1-benzyl-4-ethoxycarbonylpiperidin-3-one with 1,5-bis(2-formylphenoxy)-3-oxapentane and ammonium acetate. The molecule comprises a pentacyclic system containing the aza-14-crown-4-ether macrocycle, tetrahydropyrimidine, tetrahydropyridine and two benzene rings. The aza-14-crown-4-ether ring adopts a bowl conformation with a dihedral angle of 62.37 (5)° between the benzene rings. The tetrahydropyrimidine ring has an envelope conformation with the chiral C atom as the flap, whereas the tetrahydropyridine ring adopts a distorted chair conformation. Two amino groups are involved in intramolecular N-H...O hydrogen bonds. In the crystal, weak C-H...O hydrogen bonds link the molecules into layers parallel to the ab plane.

Related literature

For general background to the design, synthesis, chemical properties and applications of macrocyclic ligands for coordination chemistry, see: Hiraoka (1982[Hiraoka, M. (1982). In Crown Compounds. Their Characteristic and Application. Tokyo: Kodansha.]); Pedersen (1988[Pedersen, C. J. (1988). Angew. Chem. Int. Ed. Engl. 27, 1053-1083.]); Gokel & Murillo (1996[Gokel, G. W. & Murillo, O. (1996). Acc. Chem. Res. 29, 425-432.]); Bradshaw & Izatt (1997[Bradshaw, J. S. & Izatt, R. M. (1997). Acc. Chem. Res. 30, 338-345.]). For the crystal structures of related compounds, see: Levov et al. (2006[Levov, A. N., Strokina, V. M., Komarova, A. I., Anh, L. T., Soldatenkov, A. T. & Khrustalev, V. N. (2006). Mendeleev Commun. pp. 35-37.], 2008[Levov, A. N., Komarova, A. I., Soldatenkov, A. T., Avramenko, G. V., Soldatova, S. A. & Khrustalev, V. N. (2008). Russ. J. Org. Chem. 44, 1665-1670.]); Komarova et al. (2008[Komarova, A. I., Levov, A. N., Soldatenkov, A. T. & Soldatova, S. A. (2008). Chem. Heterocycl. Compd, 44, 624-625.]); Anh et al. (2008[Anh, L. T., Levov, A. N., Soldatenkov, A. T., Gruzdev, R. D. & Hieu, T. H. (2008). Russ. J. Org. Chem. 44, 463-465.], 2012a[Anh, L. T., Hieu, T. H., Soldatenkov, A. T., Soldatova, S. A. & Khrustalev, V. N. (2012a). Acta Cryst. E68, o1386-o1387.],b[Anh, L. T., Hieu, T. H., Soldatenkov, A. T., Kolyadina, N. M. & Khrustalev, V. N. (2012b). Acta Cryst. E68, o1588-o1589.],c[Anh, L. T., Hieu, T. H., Soldatenkov, A. T., Kolyadina, N. M. & Khrustalev, V. N. (2012c). Acta Cryst. E68, o2165-o2166.]); Hieu et al. (2009[Hieu, T. H., Anh, L. T., Levov, A. N., Nikitina, E. V. & Soldatenkov, A. T. (2009). Chem. Heterocycl. Compd, 45, 1406-1407.], 2011[Hieu, T. H., Anh, L. T., Soldatenkov, A. T., Golovtsov, N. I. & Soldatova, S. A. (2011). Chem. Heterocycl. Compd, 47, 1307-1308.], 2012a[Hieu, T. H., Anh, L. T., Soldatenkov, A. T., Kolyadina, N. M. & Khrustalev, V. N. (2012a). Acta Cryst. E68, o2431-o2432.],b[Hieu, T. H., Anh, L. T., Soldatenkov, A. T., Kurilkin, V. V. & Khrustalev, V. N. (2012b). Acta Cryst. E68, o2848-o2849.]); Khieu et al. (2011[Khieu, T. H., Soldatenkov, A. T., Anh, L. T., Levov, A. N., Smol'yakov, A. F., Khrustalev, V. N. & Antipin, M. Yu. (2011). Russ. J. Org. Chem. 47, 766-770.]); Sokol et al. (2011[Sokol, V. I., Kolyadina, N. M., Kvartalov, V. B., Sergienko, V. S., Soldatenkov, A. T. & Davydov, V. V. (2011). Russ. Chem. Bull. 60, 2086-2088.]).

[Scheme 1]

Experimental

Crystal data
  • C33H35N3O5

  • Mr = 553.64

  • Monoclinic, P 21

  • a = 10.5304 (5) Å

  • b = 12.6363 (5) Å

  • c = 10.7246 (5) Å

  • [beta] = 92.865 (1)°

  • V = 1425.29 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 100 K

  • 0.30 × 0.24 × 0.21 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.974, Tmax = 0.982

  • 18837 measured reflections

  • 8289 independent reflections

  • 6878 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.094

  • S = 1.00

  • 8289 reflections

  • 377 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N24-H24...O1' 0.882 (18) 2.015 (18) 2.6928 (16) 132.8 (15)
N25-H25...O14 0.882 (18) 2.441 (17) 2.9744 (17) 119.3 (13)
C6-H6...O1'i 0.95 2.42 3.3516 (19) 168
C18-H18...O1'ii 0.95 2.42 3.3613 (19) 174
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+2]; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5393 ).


Acknowledgements

We thank the National Foundation for Science and Technology Development (NAFOSTED), Hanoi, Vietnam (grant No. 104.02-2012.44) 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] [details]
Anh, L. T., Hieu, T. H., Soldatenkov, A. T., Kolyadina, N. M. & Khrustalev, V. N. (2012c). Acta Cryst. E68, o2165-o2166.  [CSD] [CrossRef] [details]
Anh, L. T., Hieu, T. H., Soldatenkov, A. T., Soldatova, S. A. & Khrustalev, V. N. (2012a). Acta Cryst. E68, o1386-o1387.  [CSD] [CrossRef] [details]
Anh, L. T., Levov, A. N., Soldatenkov, A. T., Gruzdev, R. D. & Hieu, T. H. (2008). Russ. J. Org. Chem. 44, 463-465.
Bradshaw, J. S. & Izatt, R. M. (1997). Acc. Chem. Res. 30, 338-345.  [CrossRef] [ChemPort] [ISI]
Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Gokel, G. W. & Murillo, O. (1996). Acc. Chem. Res. 29, 425-432.  [CrossRef] [ChemPort] [ISI]
Hieu, T. H., Anh, L. T., Levov, A. N., Nikitina, E. V. & Soldatenkov, A. T. (2009). Chem. Heterocycl. Compd, 45, 1406-1407.  [CrossRef] [ChemPort]
Hieu, T. H., Anh, L. T., Soldatenkov, A. T., Golovtsov, N. I. & Soldatova, S. A. (2011). Chem. Heterocycl. Compd, 47, 1307-1308.
Hieu, T. H., Anh, L. T., Soldatenkov, A. T., Kolyadina, N. M. & Khrustalev, V. N. (2012a). Acta Cryst. E68, o2431-o2432.  [CSD] [CrossRef] [details]
Hieu, T. H., Anh, L. T., Soldatenkov, A. T., Kurilkin, V. V. & Khrustalev, V. N. (2012b). Acta Cryst. E68, o2848-o2849.  [CSD] [CrossRef] [details]
Hiraoka, M. (1982). In Crown Compounds. Their Characteristic and Application. Tokyo: Kodansha.
Khieu, T. H., Soldatenkov, A. T., Anh, L. T., Levov, A. N., Smol'yakov, A. F., Khrustalev, V. N. & Antipin, M. Yu. (2011). Russ. J. Org. Chem. 47, 766-770.  [ISI] [CrossRef] [ChemPort]
Komarova, A. I., Levov, A. N., Soldatenkov, A. T. & Soldatova, S. A. (2008). Chem. Heterocycl. Compd, 44, 624-625.  [ISI] [CrossRef] [ChemPort]
Levov, A. N., Komarova, A. I., Soldatenkov, A. T., Avramenko, G. V., Soldatova, S. A. & Khrustalev, V. N. (2008). Russ. J. Org. Chem. 44, 1665-1670.  [ISI] [CrossRef] [ChemPort]
Levov, A. N., Strokina, V. M., Komarova, A. I., Anh, L. T., Soldatenkov, A. T. & Khrustalev, V. N. (2006). Mendeleev Commun. pp. 35-37.  [ISI] [CSD] [CrossRef]
Pedersen, C. J. (1988). Angew. Chem. Int. Ed. Engl. 27, 1053-1083.  [CrossRef] [ISI]
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sokol, V. I., Kolyadina, N. M., Kvartalov, V. B., Sergienko, V. S., Soldatenkov, A. T. & Davydov, V. V. (2011). Russ. Chem. Bull. 60, 2086-2088.  [ISI] [CrossRef]


Acta Cryst (2013). E69, o565-o566   [ doi:10.1107/S1600536813007241 ]

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