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Volume 69 
Part 10 
Page o1583  
October 2013  

Received 11 June 2013
Accepted 17 September 2013
Online 25 September 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.007 Å
R = 0.038
wR = 0.097
Data-to-parameter ratio = 8.4
Details
Open access

(E)-2-{[1-(3,11-Dimethyl-4-methylene-10-oxo-1-phenyl-4,5,10,11-tetrahydro-1H-benzo[b]pyrazolo[3,4-f][1,5]diazocin-5-yl)ethylidene]amino}-N-methyl-N-(3-methyl-1-phenyl-1H-pyrazol-5-yl)benzamide

aDepartment of Pharmaceutical Sciences, University of Milano, via L. Mangiagalli, 25, 20133-Milano, Italy, and bDipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche, University of Palermo, via Archirafi, 32, 90123-Palermo, Italy
Correspondence e-mail: fiorella.meneghetti@unimi.it

The central eight-membered ring of the title compound, C40H36N8O2, deviates from the ideal boat conformation because the bond between the exo-ethylene group and the adjacent N atom is twisted by 60.0 (4)° due to steric hindrance. Its adjacent benzene and pyrazole rings are oriented almost perpendicular to each other, making a dihedral angle of 85.8 (3)°. In the crystal, the molecules are linked by C(ar)-H...O hydrogen bonds, generating a three-dimensional network.

Related literature

For the synthetic method, see: Plescia et al. (1979[Plescia, S., Daidone, G. & Sprio, V. (1979). J. Heterocycl. Chem. 16, 935-937.], 1983[Plescia, S., Daidone, G. & Sprio, V. (1983). Boll. Chim. Farm. 122, 190-195.]). For background to the bioactivity of benzodiazocine derivatives, see: Milkowski et al. (1985[Milkowski, W., Liepmann, H., Zeugner, H., Ruhland, M. & Tulp, M. (1985). Eur. J. Med. Chem. 20, 345-358.]); Heitmann et al. (1988[Heitmann, W., Liepmann, H., Maetzel, U., Zeugner, H., Fuchs, A. M., Kraehling, H., Ruhland, M., Mol, F. & Tulp, M. (1988). Eur. J. Med. Chem. 23, 249-256.]).

[Scheme 1]

Experimental

Crystal data
  • C40H36N8O2

  • Mr = 660.77

  • Monoclinic, C c

  • a = 13.148 (5) Å

  • b = 28.640 (7) Å

  • c = 9.757 (4) Å

  • [beta] = 100.19 (2)°

  • V = 3616 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 293 K

  • 0.6 × 0.5 × 0.4 mm

Data collection
  • Enraf-Nonius TurboCAD-4 diffractometer

  • 3952 measured reflections

  • 3787 independent reflections

  • 2014 reflections with I > 2[sigma](I)

  • Rint = 0.039

  • 3 standard reflections every 120 min intensity decay: -3%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.097

  • S = 0.91

  • 3787 reflections

  • 453 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.])

  • Absolute structure parameter: 0.00 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C15-H15...O2i 0.93 2.57 3.173 (6) 124 (3)
C36-H36...O1ii 0.93 2.55 3.409 (6) 153 (3)
Symmetry codes: (i) [x, -y, z-{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996[Harms, K. & Wocadlo, S. (1996). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2108 ).


Acknowledgements

The authors thank MIUR for financial support. Financial support from the Fondo di Finanziamento della Ricerca (ex 60%) dell'Ateneo di Palermo is gratefully acknowledged.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [IUCr Journals]
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Harms, K. & Wocadlo, S. (1996). XCAD4. University of Marburg, Germany.
Heitmann, W., Liepmann, H., Maetzel, U., Zeugner, H., Fuchs, A. M., Kraehling, H., Ruhland, M., Mol, F. & Tulp, M. (1988). Eur. J. Med. Chem. 23, 249-256.  [CrossRef] [ChemPort] [Web of Science]
Milkowski, W., Liepmann, H., Zeugner, H., Ruhland, M. & Tulp, M. (1985). Eur. J. Med. Chem. 20, 345-358.  [ChemPort]
Plescia, S., Daidone, G. & Sprio, V. (1979). J. Heterocycl. Chem. 16, 935-937.  [CrossRef] [ChemPort]
Plescia, S., Daidone, G. & Sprio, V. (1983). Boll. Chim. Farm. 122, 190-195.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1583  [ doi:10.1107/S1600536813025671 ]

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