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Volume 69 
Part 7 
Pages o1045-o1046  
July 2013  

Received 26 May 2013
Accepted 3 June 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.048
wR = 0.141
Data-to-parameter ratio = 17.8
Details
Open access

2-Methyl-4-(naphthalen-2-yl)-3a-nitro-3,3a,4,9b-tetrahydro-2H-spiro[chromeno[3,4-c]pyrrole-1,3'-indolin]-2'-one

aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: shirai2011@gmail.com

In the title compound, C29H23N3O4, the 2-methylpyrrolidine ring adopts a twist conformation on the N-C bond involving the spiro C atom, while the hydropyran ring adopts an envelope conformation with the methine C atom bonded to the O atom as the flap. The mean plane of the indoline-2-one ring system is almost perpendicular to the mean plane of the pyrrolidine ring, making a dihedral angle of 89.73 (8)°. The latter ring makes dihedral angles of 47.80 (8) with the naphthalene ring system and 32.38 (8)° with the hydropyran ring mean plane. There is an intramolecular C-H...O hydrogen bond involving the indoline-2-one O atom. In the crystal, adjacent molecules are linked via N-H...O hydrogen bonds, forming chains propagating along [100]. The chains are linked via weak C-H...O hydrogen bonds, forming two-dimensional networks, lying parallel to (101), and consolidated by C-H...[pi] interactions.

Related literature

For the biological importance of 4H-chromene derivatives, see: Cai (2007[Cai, S. X. (2007). Recent Patents Anticancer Drug Discov. 2, 79-101.], 2008[Cai, S. X. (2008). Bioorg. Med. Chem. Lett. 18, 603-607.]); Cai et al. (2006[Cai, S. X., Drewe, J. & Kasibhatla, S. (2006). Curr. Med. Chem. 13, 2627-2644.]); Gabor (1988[Gabor, M. (1988). The Pharmacology of Benzopyrone Derivatives and Related Compounds, pp. 91-126. Budapest: Akademiai Kiado.]); Brooks (1998[Brooks, G. T. (1998). Pestic. Sci. 22, 41-50.]); Valenti et al. (1993[Valenti, P., Da Re, P., Rampa, A., Montanari, P., Carrara, M. & Cima, L. (1993). Anticancer Drug. Des. 8, 349-360.]); Hyana & Saimoto (1987[Hyana, T. & Saimoto, H. (1987). Jpn. Patent JP 621 812 768.]); Tang et al. (2007[Tang, Q.-G., Wu, W.-Y., He, W., Sun, H.-S. & Guo, C. (2007). Acta Cryst. E63, o1437-o1438.]). For applications of indoline-2-one and its derivatives as precursors in the synthesis of pharmaceuticals, see: Colgan et al. (1996[Colgan, S. T., Haggan, G. R. & Reed, R. H. (1996). J. Pharm. Biomed. Anal. 14, 825-833.]).

[Scheme 1]

Experimental

Crystal data
  • C29H23N3O4

  • Mr = 477.50

  • Monoclinic, P 21 /n

  • a = 9.4359 (6) Å

  • b = 16.5086 (11) Å

  • c = 15.1964 (10) Å

  • [beta] = 96.363 (4)°

  • V = 2352.6 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 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, U. S. A.]) Tmin = 0.973, Tmax = 0.982

  • 22349 measured reflections

  • 5856 independent reflections

  • 3862 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.141

  • S = 1.03

  • 5856 reflections

  • 329 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10-C14/C19 ring.

D-H...A D-H H...A D...A D-H...A
C9-H9...O4 0.98 2.44 3.250 (2) 140
N3-H3A...O3i 0.87 (2) 2.52 (2) 3.220 (2) 138 (2)
C2-H2...O3ii 0.93 2.58 3.156 (2) 121
C3-H3...Cg1ii 0.93 2.57 3.473 (2) 164
Symmetry codes: (i) x-1, y, 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, U. S. A.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]); 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: SU2607 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. SK, TS and DV thank the UGC (SAP-CAS) for the departmental facilities. SK also thanks DST PURSE for a Junior Research Fellowship and TS also thanks DST Inspire for a fellowship.

References

Brooks, G. T. (1998). Pestic. Sci. 22, 41-50.  [CrossRef]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.
Cai, S. X. (2007). Recent Patents Anticancer Drug Discov. 2, 79-101.
Cai, S. X. (2008). Bioorg. Med. Chem. Lett. 18, 603-607.  [PubMed]
Cai, S. X., Drewe, J. & Kasibhatla, S. (2006). Curr. Med. Chem. 13, 2627-2644.  [Web of Science] [PubMed] [ChemPort]
Colgan, S. T., Haggan, G. R. & Reed, R. H. (1996). J. Pharm. Biomed. Anal. 14, 825-833.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gabor, M. (1988). The Pharmacology of Benzopyrone Derivatives and Related Compounds, pp. 91-126. Budapest: Akademiai Kiado.
Hyana, T. & Saimoto, H. (1987). Jpn. Patent JP 621 812 768.
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]
Tang, Q.-G., Wu, W.-Y., He, W., Sun, H.-S. & Guo, C. (2007). Acta Cryst. E63, o1437-o1438.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Valenti, P., Da Re, P., Rampa, A., Montanari, P., Carrara, M. & Cima, L. (1993). Anticancer Drug. Des. 8, 349-360.  [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1045-o1046   [ doi:10.1107/S160053681301533X ]

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