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Volume 69 
Part 5 
Pages o746-o747  
May 2013  

Received 8 March 2013
Accepted 11 April 2013
Online 17 April 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.049
wR = 0.147
Data-to-parameter ratio = 20.8
Details
Open access

4'-(4-Fluorophenyl)-1'-methyldispiro[indane-2,2'-pyrrolidine-3',2''-indane]-1,3,1''-trione methanol hemisolvate

aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bFaculty of Pharmaceutical Science, UCSI (University College Sedaya International) University, Kuala Lumpur, Malaysia, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: arazaki@usm.my

The asymmetric unit of the title compound, C29H24FNO5·0.5CH3OH, contains two independent molecules and a one methanol solvent molecule. The methanol molecule is O-H...O hydrogen bonded to one of the independent molecules. The pyrrolidine rings in both molecules adopt half-chair conformations, while the cyclopentane rings within the indane groups are in flattened envelope conformations, with the spiro C atoms forming the flaps. The benzene rings of the indane ring systems form a dihedral angle of 35.06 (7)° in one independent molecule and 31.16 (8)° in the other. The fluoro-substituted benzene ring forms dihedral angles of 65.35 (6) and 85.87 (7)° with the indane group benzene rings in one molecule, and 72.78 (8) and 77.27 (8)° in the other. In each molecule, a weak intramolecular C-H...O hydrogen bond forms an S(6) ring motif. In the crystal, weak C-H...O, C-H...N and C-H...F hydrogen bonds link the molecules into a three-dimensional network.

Related literature

For background to compounds with antitubercular activity, see: Ali et al. (2011[Ali, M. A., Ismail, R., Choon, T. S., Pandian, S. & Ansari, M. Z. H. (2011). J. Enzyme Inhib. Med. Chem. 26, 598-602.]). For related structures, see: Wei et al. (2011[Wei, A. C., Ali, M. A., Yoon, Y. K., Quah, C. K. & Fun, H.-K. (2011). Acta Cryst. E67, o3274.], 2012[Wei, A. C., Ali, M. A., Choon, T. S., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o1265-o1266.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C29H24FNO5·0.5CH4O

  • Mr = 501.52

  • Monoclinic, P 21 /c

  • a = 14.6385 (6) Å

  • b = 12.5099 (6) Å

  • c = 26.2017 (10) Å

  • [beta] = 92.645 (1)°

  • V = 4793.1 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.44 × 0.21 × 0.15 mm

Data collection
  • Bruker APEX DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.957, Tmax = 0.985

  • 53390 measured reflections

  • 14094 independent reflections

  • 10283 reflections with I > 2[sigma](I)

  • Rint = 0.046

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.147

  • S = 1.04

  • 14094 reflections

  • 678 parameters

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

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O6-H1O6...O4A 0.97 (3) 1.99 (3) 2.9346 (18) 164 (3)
C8A-H8AA...O5A 0.99 2.43 3.088 (2) 124
C8B-H8BA...O5B 0.99 2.38 3.0960 (19) 128
C26A-H26A...O5Ai 0.95 2.54 3.2430 (18) 131
C27A-H27A...N1Bii 0.98 2.42 3.337 (2) 155
C28A-H28A...O2Biii 0.98 2.50 3.3478 (19) 145
C28B-H28F...O6iv 0.98 2.46 3.360 (2) 153
C30-H30B...F1Av 0.98 2.53 3.307 (2) 136
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) -x+2, -y+2, -z+2; (iv) x+1, y, z; (v) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL 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: LH5596 ).


Acknowledgements

The authors wish to express their gratitude and appreciation to the Pharmacogenetics and Novel Therapeutics Research Cluster, Institute for Research in Molecular Medicine, Universiti Sains Malaysia (USM), Penang, for support of this work. This work was funded through Research Grant No. RUC (1001/PSK/8620012) and HiCoE Research Grant No (311.CIPPM.4401005). IAR also thanks USM for the Short Term Grant, No. 304/PFIZIK/6312078.

References

Ali, M. A., Ismail, R., Choon, T. S., Pandian, S. & Ansari, M. Z. H. (2011). J. Enzyme Inhib. Med. Chem. 26, 598-602.  [ISI] [CrossRef] [ChemPort] [PubMed]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
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]
Wei, A. C., Ali, M. A., Choon, T. S., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o1265-o1266.  [CSD] [CrossRef] [ChemPort] [details]
Wei, A. C., Ali, M. A., Yoon, Y. K., Quah, C. K. & Fun, H.-K. (2011). Acta Cryst. E67, o3274.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o746-o747   [ doi:10.1107/S1600536813009987 ]

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