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Volume 69 
Part 7 
Pages o1023-o1024  
July 2013  

Received 14 May 2013
Accepted 28 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.048
wR = 0.136
Data-to-parameter ratio = 21.8
Details
Open access

(1R*,21S*,22R*,24S*)-Methyl ethyl 2-[23-hydroxy-22,24-diphenyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.02,7.015,20]pentacosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate

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, Russian Federation, 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, C40H41NO8, is a product of the reduction of the cyclic carbonyl group of the [gamma]-piperidone subunit of the aza-14-crown-4 ether with subsequent re-esterification of its dimethyl butenoate substituent into a monoethyl monomethyl group. The azacrown macrocycle exhibits a bowl conformation with a dihedral angle of 70.82 (5)° between the benzene rings fused to it. The piperidine ring adopts a chair conformation and the methyl ethyl ethylenedicarboxylate fragment has a cis conformation, with a dihedral angle of 66.51 (7)° between the two carboxylate groups. The ethyl group is disordered over two sites with occupancies of 0.70 (1):0.30 (1). In the crystal, molecules form inversion dimers, via pairs of O-H...O hydrogen bonds, that stack along the a axis.

Related literature

For the synthesis of azacrown ethers of this type, 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. 16, 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.]); 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.]); Hieu et al. (2011[Hieu, T. H., Anh, L. T., Soldatenkov, A. T., Golovtsov, N. I. & Soldatova, S. A. (2011). Chem. Heterocycl. Compd, 47, 1307-1308.]); Khieu et al. (2011[Khieu, C. K., 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.]). For the structures of related compounds, see: Anh et al. (2012a[Anh, L. T., Hieu, T. H., Soldatenkov, A. T., Kolyadina, N. M. & Khrustalev, V. N. (2012a). Acta Cryst. E68, o1588-o1589.],b[Anh, L. T., Hieu, T. H., Soldatenkov, A. T., Soldatova, S. A. & Khrustalev, V. N. (2012b). Acta Cryst. E68, o1386-o1387.]); Hieu et al. (2012[Hieu, T. H., Anh, L. T., Soldatenkov, A. T., Kolyadina, N. M. & Khrustalev, V. N. (2012). Acta Cryst. E68, o2431-o2432.]).

[Scheme 1]

Experimental

Crystal data
  • C40H41NO8

  • Mr = 663.74

  • Monoclinic, P 21 /n

  • a = 11.6594 (4) Å

  • b = 19.3088 (6) Å

  • c = 15.8522 (5) Å

  • [beta] = 108.887 (1)°

  • V = 3376.64 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 100 K

  • 0.18 × 0.15 × 0.12 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2003[Bruker (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.984, Tmax = 0.989

  • 44045 measured reflections

  • 9846 independent reflections

  • 6852 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.136

  • S = 1.00

  • 9846 reflections

  • 452 parameters

  • 4 restraints

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

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.48 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O23-H23O...O43i 0.82 (2) 2.39 (2) 3.1109 (14) 148 (2)
Symmetry code: (i) -x+1, -y+1, -z+1.

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: RK2405 ).


Acknowledgements

We thank the National Foundation for Science and Technology Development (NAFOSTED) (grant 104.02-2012.44) for financial support of this work.

References

Anh, L. T., Hieu, T. H., Soldatenkov, A. T., Kolyadina, N. M. & Khrustalev, V. N. (2012a). Acta Cryst. E68, o1588-o1589.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Anh, L. T., Hieu, T. H., Soldatenkov, A. T., Soldatova, S. A. & Khrustalev, V. N. (2012b). Acta Cryst. E68, o1386-o1387.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Anh, L. T., Levov, A. N., Soldatenkov, A. T., Gruzdev, R. D. & Hieu, T. H. (2008). Russ. J. Org. Chem. 44, 463-465.
Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
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. (2012). Acta Cryst. E68, o2431-o2432.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Khieu, C. K., 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.  [Web of Science] [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.  [Web of Science] [CrossRef] [ChemPort]
Levov, A. N., Strokina, V. M., Komarova, A. I., Anh, L. T., Soldatenkov, A. T. & Khrustalev, V. N. (2006). Mendeleev Commun. 16, 35-37.  [Web of Science] [CSD] [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1023-o1024   [ doi:10.1107/S1600536813014748 ]

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