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Volume 69 
Part 7 
Page o1055  
July 2013  

Received 2 May 2013
Accepted 30 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.132
Data-to-parameter ratio = 21.4
Details
Open access

Methyl 4-anilino-2',5-dioxo-1',2'-dihydro-5H-spiro[furan-2,3'-indole]-3-carboxylate

aDepartment of Physics, Ethiraj College for Women (Autonomous), Chennai 600 008, India,bDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and cOrganic Chemistry Division, Central Leather Research Institute, Adyar, Chennai 600 020, India
Correspondence e-mail: ksethusankar@yahoo.co.in

In the title compound, C19H14N2O5, the spiro junction links an oxindole moeity and a furan ring, which subtend a dihedral angle of 83.49 (6)°. The molecular structure features an N-H...O hydrogen bond, which generates an S(6) ring motif. The crystal packing is governed by two N-H...O interactions, one of which generates a centrosymmetric R22(14) dimer. The other N-H...O interaction along with a C-H...O hydrogen bond contributes to the formation of a C22[R22(9)] dimeric chain running along the b-axis direction.

Related literature

For applications of spiro oxindoles, see: Kornet & Thio (1976[Kornet, M. J. & Thio, A. P. (1976). J. Med. Chem. 19, 892-898.]); Kobayashi et al. (1991[Kobayashi, J., Tsuda, M., Agemi, K., Shigemori, H., Ishibashi, M., Sasaki, T. & Mikami, Y. (1991). Tetrahedron, 47, 6617-6622.]). For applications of furans, see: Schoop et al. (2000[Schoop, A., Grieving, H. & Gohrt, A. (2000). Tetrahedron Lett. 41, 1913-1916.]). For puckering and asymmetry parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For a related structure, see: Gayathri et al. (2006[Gayathri, D., Velmurugan, D., Ravikumar, K., Savitha, G. & Perumal, P. T. (2006). Acta Cryst. E62, o5947-o5949.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C19H14N2O5

  • Mr = 350.32

  • Monoclinic, P 21 /c

  • a = 12.1713 (6) Å

  • b = 13.6144 (7) Å

  • c = 10.9602 (6) Å

  • [beta] = 114.813 (2)°

  • V = 1648.50 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U.S.A.]) Tmin = 0.969, Tmax = 0.979

  • 20901 measured reflections

  • 5167 independent reflections

  • 3502 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.132

  • S = 1.00

  • 5167 reflections

  • 242 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O5i 0.89 (2) 2.19 (2) 3.0268 (16) 157 (2)
N2-H2A...O1ii 0.89 (1) 2.19 (1) 2.9907 (17) 149 (1)
N2-H2A...O5 0.89 (1) 2.39 (2) 2.9691 (16) 123 (1)
C13-H13A...O1iii 0.96 2.41 3.2999 (18) 153
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) -x+1, -y+1, -z+2; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); 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: RK2403 ).


Acknowledgements

The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U.S.A.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [IUCr Journals]
Gayathri, D., Velmurugan, D., Ravikumar, K., Savitha, G. & Perumal, P. T. (2006). Acta Cryst. E62, o5947-o5949.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Kobayashi, J., Tsuda, M., Agemi, K., Shigemori, H., Ishibashi, M., Sasaki, T. & Mikami, Y. (1991). Tetrahedron, 47, 6617-6622.  [CrossRef] [ChemPort] [Web of Science]
Kornet, M. J. & Thio, A. P. (1976). J. Med. Chem. 19, 892-898.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Schoop, A., Grieving, H. & Gohrt, A. (2000). Tetrahedron Lett. 41, 1913-1916.  [Web of Science] [CSD] [CrossRef] [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, o1055  [ doi:10.1107/S1600536813014967 ]

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