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Volume 68 
Part 5 
Page o1481  
May 2012  

Received 17 March 2012
Accepted 16 April 2012
Online 21 April 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.062
wR = 0.188
Data-to-parameter ratio = 15.1
Details
Open access

2,4,6,8-Tetrakis(4-chlorophenyl)-3,7-diazabicyclo[3.3.1]nonan-9-one O-benzyloxime acetone monosolvate

aDepartment of Biomedicinal Chemistry, Inje University, Gimhae, Gyeongnam 621 749, Republic of Korea, and bDepartment of Chemistry, IIT Madras, Chennai 600 036, TamilNadu, India
Correspondence e-mail: parthisivam@yahoo.co.in

In the title compound, C38H31Cl4N3O·C3H6O, the 3,7-diaza-bicycle exists in a chair-boat conformation. The 4-chlorophenyl groups attached to the chair form are equatorially oriented at an angle of 18.15 (3)° with respect to each other, whereas the 4-chlorophenyl groups attached to the boat form are oriented at an angle of 32.64 (3)°. In the crystal, molecules are linked by N-H...[pi] and C-H...O interactions.

Related literature

For the synthesis and stereochemistry of 3,7-diazabicyclo[3.3.1]nonan-9-one derivatives, see: Parthiban et al. (2008[Parthiban, P., Ramachandran, R., Aridoss, G. & Kabilan, S. (2008). Magn. Reson. Chem. 46, 780-785.]). For the biological activity of 3,7-diazabicyclo[3.3.1]nonan-9-one derivatives and related structures, see: Parthiban et al. (2009[Parthiban, P., Aridoss, G., Rathika, P., Ramkumar, V. & Kabilan, S. (2009). Bioorg. Med. Chem. Lett. 19, 6981-6985.], 2010[Parthiban, P., Kabilan, S., Ramkumar, V. & Jeong, Y. T. (2010). Bioorg. Med. Chem. Lett. 20, 6452-6458.]); Asakawa (1995[Asakawa, Y. (1995). In Progress in the Chemistry of Organic Natural Products, edited by G. W. Moore, R. E. Steglich & W. Tamm. New York: Springer-Verlag.]); Jayaraman & Avila (1981[Jayaraman, R. & Avila, S. (1981). Chem. Rev. 81, 149-174.]). For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]); Nardelli (1983[Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.]); Luger & Bülow (1983[Luger, P. & Bülow, R. (1983). J. Appl. Cryst. 16, 431-432.]).

[Scheme 1]

Experimental

Crystal data
  • C38H31Cl4N3O·C3H6O

  • Mr = 745.54

  • Monoclinic, P 21 /n

  • a = 14.9237 (5) Å

  • b = 10.5064 (3) Å

  • c = 24.6015 (7) Å

  • [beta] = 93.116 (1)°

  • V = 3851.7 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.35 mm-1

  • T = 293 K

  • 0.20 × 0.16 × 0.16 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.934, Tmax = 0.947

  • 35931 measured reflections

  • 7173 independent reflections

  • 4263 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.188

  • S = 1.03

  • 7173 reflections

  • 475 parameters

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

  • [Delta][rho]max = 0.89 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C8-C13 ring.

D-H...A D-H H...A D...A D-H...A
C13-H13...O2 0.93 2.52 3.441 (6) 172
N2-H2A...Cg3i 0.88 (3) 2.85 (3) 3.637 (3) 150 (3)
Symmetry code: (i) [-x+{\script{1\over 2}}, y+{\script{3\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SIR92 (Altomare et al., 1993)[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6689 ).


Acknowledgements

This research was supported by the National Research Foundation (NRF) of Korea.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [ISI] [details]
Asakawa, Y. (1995). In Progress in the Chemistry of Organic Natural Products, edited by G. W. Moore, R. E. Steglich & W. Tamm. New York: Springer-Verlag.
Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Jayaraman, R. & Avila, S. (1981). Chem. Rev. 81, 149-174.
Luger, P. & Bülow, R. (1983). J. Appl. Cryst. 16, 431-432.  [CrossRef] [ChemPort] [ISI] [details]
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.  [CrossRef] [details]
Parthiban, P., Aridoss, G., Rathika, P., Ramkumar, V. & Kabilan, S. (2009). Bioorg. Med. Chem. Lett. 19, 6981-6985.  [CSD] [CrossRef] [PubMed] [ChemPort]
Parthiban, P., Kabilan, S., Ramkumar, V. & Jeong, Y. T. (2010). Bioorg. Med. Chem. Lett. 20, 6452-6458.  [CSD] [CrossRef] [ChemPort] [PubMed]
Parthiban, P., Ramachandran, R., Aridoss, G. & Kabilan, S. (2008). Magn. Reson. Chem. 46, 780-785.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o1481  [ doi:10.1107/S1600536812016509 ]

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