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Volume 69 
Part 6 
Pages o823-o824  
June 2013  

Received 26 March 2013
Accepted 27 April 2013
Online 4 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.041
wR = 0.123
Data-to-parameter ratio = 17.9
Details
Open access

Methyl (3S,10b'S)-5-chloro-9'-fluoro-1-methyl-2-oxo-5'-phenyl-10b'H-spiro[indoline-3,1'-pyrazolo[3,2-a]isoquinoline]-2'-carboxylate

aDepartment of Physics, S.M.K. Fomra Institute of Technology, Thaiyur, Chennai 603 103, India,bIndustrial Chemistry Laboratory, Central Leather Research Institute, Adyar, Chennai 600 020, India, and cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India
Correspondence e-mail: a_sp59@yahoo.in

In the title compound, C27H19ClFN3O3, the pyrazole ring has a twist conformation and the six-membered ring to which it is fused has a screw-boat conformation. The mean plane of the pyrazole ring is inclined to the 2-methylindoline ring by 85.03 (9) and by 28.17 (8)° to the mean plane of the isoquinoline ring system. In the crystal, molecules are linked by pairs of C-H...F hydrogen bonds, forming inversion dimers. These dimers are linked via C-H...O hydrogen bonds, forming a two-dimensional network lying parallel to (10-1).

Related literature

For the biological activity of pyrazoles, see: Huang et al. (1996[Huang, R. Q., Song, J. & Feng, L. (1996). Chem. J. Chin. Univ. 17, 1089-1091.]); Li et al. (2005[Li, M., Wang, S. W., Wen, L. R., Qi, W. Y. & Yang, H. Z. (2005). Chin. J. Struct. Chem. 4, 64-68.]); Patel et al. (1990[Patel, H. V., Fernandes, P. S. & Vyas, K. A. (1990). Indian J. Chem. Sect. B, 29, 135-141.]); Zhao et al. (2001[Zhao, W. G., Li, Z. M., Yuan, P. W., Yuan, D. K., Wang, W. Y. & Wang, S. H. (2001). Chin. J. Org. Chem. 21, 593-598.]). For the crystal structures of pyrazoles, see: Manivel et al. (2009[Manivel, P. R., Hathwar, V., Maiyalagan, T., Krishnakumar, V. & Khan, F. N. (2009). Acta Cryst. E65, o1798.]); Khan et al. (2010a[Khan, F. N., Manivel, P., Kone, S., Hathwar, V. R. & Ng, S. W. (2010a). Acta Cryst. E66, o368.],b[Khan, F. N., Manivel, P., Krishnakumar, V., Hathwar, V. R. & Ng, S. W. (2010b). Acta Cryst. E66, o369.],c[Khan, F. N., Manivel, P., Prabakaran, K., Hathwar, V. R. & Ng, S. W. (2010c). Acta Cryst. E66, o370.]). For the crystal structure of an isoquinazole, see: Hathwar et al. (2008[Hathwar, V. R., Prabakaran, K., Subashini, R., Manivel, P. & Khan, F. N. (2008). Acta Cryst. E64, o2295.]). For the biological activity of fused isoquinoline compounds, see: Aubry et al. (2004[Aubry, A., Pan, X. S., Fisher, L. M., Jarlier, V. & Cambau, E. (2004). Antimicrob. Agents Chemother. 48, 1281-1288.]); Marco et al. (2005[Marco, E., Laine, W., Tardy, C., Lansiaux, A., Iwao, M., Ishibashi, F., Bailly, C. & Gago, F. (2005). J. Med. Chem. 48, 3796-3807.]); Reddy et al. (1999[Reddy, M. V. R., Rao, M. R., Rhodes, D., Hansen, M. S. T., Rubins, K., Bushman, F. D., Venkateswarlu, Y. & Faulkner, D. J. (1999). J. Med. Chem. 42, 1901-1907.]). For related structures, see: Chen & Wu (2010[Chen, Z.-Y. & Wu, J. (2010). Org. Lett. 12, 4856-4859.]); Ye et al. (2010[Ye, S.-Q., Yang, X.-D. & Wu, J. (2010). Chem. Commun. pp. 5238-5240.]); Yu et al. (2011a[Yu, X.-X., Pan, X.-L. & Wu, J. (2011a). Tetrahedron, 67, 1145-1149.],b[Yu, X.-X., Yang, Q., Lou, H.-L., Peng, Y.-Y. & Wu, J. (2011b). Org. Biomol. Chem. 9, 7033-7037.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C27H19ClFN3O3

  • Mr = 487.90

  • Monoclinic, C 2/c

  • a = 15.1203 (3) Å

  • b = 21.1088 (5) Å

  • c = 15.6334 (3) Å

  • [beta] = 112.977 (1)°

  • V = 4593.85 (17) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker. (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.940, Tmax = 0.959

  • 22581 measured reflections

  • 5703 independent reflections

  • 4241 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.123

  • S = 1.03

  • 5703 reflections

  • 318 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C27-H27B...F1i 0.96 2.52 3.226 (3) 130
C14-H14...O1ii 0.93 2.50 3.402 (2) 163
Symmetry codes: (i) -x, -y+1, -z; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

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: SU2581 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and BioPhysics, University of Madras, Chennai, India, for the data collection.

References

Aubry, A., Pan, X. S., Fisher, L. M., Jarlier, V. & Cambau, E. (2004). Antimicrob. Agents Chemother. 48, 1281-1288.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bruker. (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, Z.-Y. & Wu, J. (2010). Org. Lett. 12, 4856-4859.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hathwar, V. R., Prabakaran, K., Subashini, R., Manivel, P. & Khan, F. N. (2008). Acta Cryst. E64, o2295.  [CSD] [CrossRef] [details]
Huang, R. Q., Song, J. & Feng, L. (1996). Chem. J. Chin. Univ. 17, 1089-1091.  [ChemPort]
Khan, F. N., Manivel, P., Kone, S., Hathwar, V. R. & Ng, S. W. (2010a). Acta Cryst. E66, o368.  [CSD] [CrossRef] [details]
Khan, F. N., Manivel, P., Krishnakumar, V., Hathwar, V. R. & Ng, S. W. (2010b). Acta Cryst. E66, o369.  [CSD] [CrossRef] [details]
Khan, F. N., Manivel, P., Prabakaran, K., Hathwar, V. R. & Ng, S. W. (2010c). Acta Cryst. E66, o370.  [CSD] [CrossRef] [details]
Li, M., Wang, S. W., Wen, L. R., Qi, W. Y. & Yang, H. Z. (2005). Chin. J. Struct. Chem. 4, 64-68.
Manivel, P. R., Hathwar, V., Maiyalagan, T., Krishnakumar, V. & Khan, F. N. (2009). Acta Cryst. E65, o1798.  [CSD] [CrossRef] [details]
Marco, E., Laine, W., Tardy, C., Lansiaux, A., Iwao, M., Ishibashi, F., Bailly, C. & Gago, F. (2005). J. Med. Chem. 48, 3796-3807.  [ISI] [CrossRef] [PubMed] [ChemPort]
Patel, H. V., Fernandes, P. S. & Vyas, K. A. (1990). Indian J. Chem. Sect. B, 29, 135-141.
Reddy, M. V. R., Rao, M. R., Rhodes, D., Hansen, M. S. T., Rubins, K., Bushman, F. D., Venkateswarlu, Y. & Faulkner, D. J. (1999). J. Med. Chem. 42, 1901-1907.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Ye, S.-Q., Yang, X.-D. & Wu, J. (2010). Chem. Commun. pp. 5238-5240.  [CSD] [CrossRef]
Yu, X.-X., Pan, X.-L. & Wu, J. (2011a). Tetrahedron, 67, 1145-1149.  [ISI] [CrossRef] [ChemPort]
Yu, X.-X., Yang, Q., Lou, H.-L., Peng, Y.-Y. & Wu, J. (2011b). Org. Biomol. Chem. 9, 7033-7037.  [CSD] [CrossRef] [ChemPort] [PubMed]
Zhao, W. G., Li, Z. M., Yuan, P. W., Yuan, D. K., Wang, W. Y. & Wang, S. H. (2001). Chin. J. Org. Chem. 21, 593-598.  [ChemPort]


Acta Cryst (2013). E69, o823-o824   [ doi:10.1107/S1600536813011549 ]

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