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Volume 69 
Part 8 
Pages o1194-o1195  
August 2013  

Received 17 May 2013
Accepted 27 June 2013
Online 3 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
Disorder in solvent or counterion
R = 0.051
wR = 0.153
Data-to-parameter ratio = 15.6
Details
Open access

1'-(1,3-Diphenyl-1H-pyrazol-4-yl)-1''-(prop-2-en-1-yl)-2',3',5',6',7',7a'-hexahydro-1'H-dispiro[1-benzopyran-3,2'-pyrrolizine-3',3''-indoline]-2'',4-dione 0.75-hydrate

aDepartment of Physics, Meenakshi College of Engineering, West K.K. Nagar, Chennai 600 078, India,bIndustrial Chemistry Lab, Central Leather Research Institute, Adyar, Chennai 600 020, India, and cDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India
Correspondence e-mail: ksethusankar@yahoo.co.in

In the central aza-bicyclooctane unit of the title compound, C40H34N4O3·0.75H2O, the peripheral pyrrolidine ring adopts an envelope conformation with the N atom deviating by 0.209 (2) Å, whereas the other pyrrolidine ring adopts a twisted conformation with the bridging N and C atoms deviating by -0.218 (2) and 0.236 (3) Å, respectively, from the rest of the ring. The pyrazole ring forms dihedral angles of 42.36 (7) and 24.07 (8)° with its C- and N-attached phenyl groups, respectively. The solvent water molecule has a partial occupancy of 0.75. In the crystal, the water molecules link the fused-ring molecules into chains along the b axis via O-H...N and O-H...O hydrogen bonds. The crystal packing is further stabilized by C-H...[pi] interactions involving a methylene group of the pyran ring and the C-attached benzene ring on the pyrazole ring.

Related literature

For the biological activity of pyrazole derivatives, see: Mahajan et al. (1991[Mahajan, R. N., Havaldar, F. H. & Fernandes, P. S. (1991). J. Indian Chem. Soc. 68, 245-249.]); Baraldi et al. (1998[Baraldi, P. G., Manfredini, S., Romagnoli, R., Stevanato, L., Zaid, A. N. & Manservigi, R. (1998). Nucleosides Nucleotides, 17, 2165-2171.]); Katayama & Oshiyama (1997[Katayama, H. & Oshiyama, T. (1997). Can. J. Chem. 75, 913-919.]); Chen & Li (1998[Chen, H. S. & Li, Z. M. (1998). Chem. J. Chin. Univ. 19, 572-576.]). For a related structure, see: Jagadeesan et al. (2013[Jagadeesan, G., Sethusankar, K., Kathirvelan, D., Haribabu, J. & Reddy, B. S. R. (2013). Acta Cryst. E69, o317.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C40H34N4O3·0.75H2O

  • Mr = 632.22

  • Monoclinic, P 21 /n

  • a = 11.451 (2) Å

  • b = 13.496 (2) Å

  • c = 20.815 (3) Å

  • [beta] = 96.206 (9)°

  • V = 3198.0 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 296 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.975, Tmax = 0.983

  • 32619 measured reflections

  • 6870 independent reflections

  • 4468 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.153

  • S = 1.02

  • 6870 reflections

  • 439 parameters

  • 3 restraints

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

  • [Delta][rho]max = 0.53 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
O4W-H1W...N3i 0.91 (2) 2.02 (3) 2.892 (4) 161 (4)
O4W-H2W...O2ii 0.90 (1) 1.96 (1) 2.841 (3) 165 (3)
C40-H40A...Cg1iii 0.97 2.78 3.540 (3) 136
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x, y+1, z; (iii) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2105 ).


Acknowledgements

The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection. KS thanks the University Grant Commission (UGC), India, for a Minor Research Project.

References

Baraldi, P. G., Manfredini, S., Romagnoli, R., Stevanato, L., Zaid, A. N. & Manservigi, R. (1998). Nucleosides Nucleotides, 17, 2165-2171.  [CrossRef] [ChemPort]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, H. S. & Li, Z. M. (1998). Chem. J. Chin. Univ. 19, 572-576.  [ChemPort]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Jagadeesan, G., Sethusankar, K., Kathirvelan, D., Haribabu, J. & Reddy, B. S. R. (2013). Acta Cryst. E69, o317.  [CSD] [CrossRef] [IUCr Journals]
Katayama, H. & Oshiyama, T. (1997). Can. J. Chem. 75, 913-919.  [CrossRef] [ChemPort] [Web of Science]
Mahajan, R. N., Havaldar, F. H. & Fernandes, P. S. (1991). J. Indian Chem. Soc. 68, 245-249.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1194-o1195   [ doi:10.1107/S160053681301773X ]

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