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Volume 69 
Part 12 
Pages o1835-o1836  
December 2013  

Received 31 October 2013
Accepted 20 November 2013
Online 30 November 2013

Key indicators
Single-crystal X-ray study
T = 130 K
Mean [sigma](C-C) = 0.009 Å
Disorder in main residue
R = 0.052
wR = 0.137
Data-to-parameter ratio = 10.5
Details
Open access

(S)-(+)-cis-4'-Benzyl­oxypraziquantel

aDepartamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, 04510 México, DF, Mexico
Correspondence e-mail: albertocedillo_cruz@hotmail.com

The asymmetric unit of the title compound, C26H30N2O3 {systematic name (S)-(+)-2-[cis-4-(benz­yloxy)cyclo­hexa­ne­carb­on­yl]-1,2,3,6,7,11b-hexa­hydro-4H-pyrazino­[2,1-a]isoquin­olin-4-one}, consists of two independent mol­ecules in which the O= Camide group is syn to the N-C(C=Olactam) moiety, making dihedral angles of 2.0 (8) and 3.7 (8)°. The conformation of the 1,4-disubstituted cyclo­hexane ring is cis in each independent mol­ecule, with the carbonyl group occupying an equatorial position and the benz­yloxy group an axial position. In one mol­ecule, two C and one O atom of the benz­yloxy group are disordered over two sets of sites, with a refined occupancy ratio of 0.772 (8):0.228 (8). In the crystal, mol­ecules are linked by C-H...O inter­actions, forming ribbons parallel to the b-axis direction.

Related literature

For pyrazinoisoquinolone derivatives with anthelmintic activity, see: Staudt et al. (1992[Staudt, U., Schmahl, G., Blaschke, G. & Mehlhorn, H. (1992). Parasitol. Res. 78, 392-397.]); Jung et al. (2008[Jung, H., Cárdenas, G., Sciutto, E. & Fleury, A. (2008). Curr. Top. Med. Chem. 8, 424-433.]); Thétiot-Laurent et al. (2013[Thétiot-Laurent, S. A. L., Boissier, J., Robert, A. & Meunier, B. (2013). Angew. Chem. Int. Ed. 52, 7936-7956.]); Duan et al. (2012[Duan, W.-W., Qiu, S.-J., Zhao, Y., Sun, H., Qiao, C. & Xia, C.-M. (2012). Bioorg. Med. Chem. Lett. 22, 1587-1590.]); Patra et al. (2013[Patra, M., Ingram, K., Pierroz, V., Ferrari, S., Spingler, B., Gasser, R. B., Keiser, J. & Gasser, G. (2013). Chem. Eur. J. 19, 2232-2235.]); Wang et al. (2013[Wang, W.-L., Song, L.-J., Chen, X., Yin, X.-R., Fan, W.-H., Wang, G.-P., Yu, C.-X. & Feng, B. (2013). Molecules, 18, 9163-9178.]); Meier & Blaschke (2001[Meier, H. & Blaschke, G. (2001). J. Pharm. Biomed. Anal. 26, 409-415.]).

[Scheme 1]

Experimental

Crystal data
  • C26H30N2O3

  • Mr = 418.52

  • Monoclinic, P 21

  • a = 15.007 (2) Å

  • b = 10.3322 (8) Å

  • c = 16.019 (2) Å

  • [beta] = 117.399 (13)°

  • V = 2205.2 (5) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.66 mm-1

  • T = 130 K

  • 0.59 × 0.31 × 0.13 mm

Data collection
  • Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer

  • Absorption correction: analytical [CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.]), based on expressions derived by Clark & Reid (1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.937, Tmax = 0.979

  • 8420 measured reflections

  • 5852 independent reflections

  • 3845 reflections with I > 2[sigma](I)

  • Rint = 0.057

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.137

  • S = 1.03

  • 5852 reflections

  • 558 parameters

  • 4 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

  • Absolute structure: Flack parameter determined using 868 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])

  • Absolute structure parameter: 0.4 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C20-H20B...O2i 0.99 2.45 3.332 (7) 149
C20A-H20C...O2Aii 0.99 2.60 3.567 (10) 165
C20B-H20F...O2Aii 0.99 2.26 3.19 (3) 156
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+1]; (ii) [-x, y+{\script{1\over 2}}, -z].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]) and ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5093 ).


Acknowledgements

AC-C is grateful to CONACyT for a graduate student scholarship. The authors acknowledge M. Flores-Alamo for the data collection.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.  [CrossRef] [IUCr Journals]
Duan, W.-W., Qiu, S.-J., Zhao, Y., Sun, H., Qiao, C. & Xia, C.-M. (2012). Bioorg. Med. Chem. Lett. 22, 1587-1590.  [CrossRef] [ChemPort] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Jung, H., Cárdenas, G., Sciutto, E. & Fleury, A. (2008). Curr. Top. Med. Chem. 8, 424-433.  [PubMed] [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Meier, H. & Blaschke, G. (2001). J. Pharm. Biomed. Anal. 26, 409-415.  [CrossRef] [PubMed] [ChemPort]
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.  [CrossRef] [ChemPort] [IUCr Journals]
Patra, M., Ingram, K., Pierroz, V., Ferrari, S., Spingler, B., Gasser, R. B., Keiser, J. & Gasser, G. (2013). Chem. Eur. J. 19, 2232-2235.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Staudt, U., Schmahl, G., Blaschke, G. & Mehlhorn, H. (1992). Parasitol. Res. 78, 392-397.  [CrossRef] [PubMed] [ChemPort]
Thétiot-Laurent, S. A. L., Boissier, J., Robert, A. & Meunier, B. (2013). Angew. Chem. Int. Ed. 52, 7936-7956.
Wang, W.-L., Song, L.-J., Chen, X., Yin, X.-R., Fan, W.-H., Wang, G.-P., Yu, C.-X. & Feng, B. (2013). Molecules, 18, 9163-9178.  [CrossRef] [ChemPort] [PubMed]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1835-o1836   [ doi:10.1107/S1600536813031735 ]

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