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Volume 69 
Part 7 
Pages o1181-o1182  
July 2013  

Received 17 June 2013
Accepted 25 June 2013
Online 29 June 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.056
wR = 0.173
Data-to-parameter ratio = 16.3
Details
Open access

(±)-3-(5-Amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)-2-benzofuran-1(3H)-one

aDepartamento de Química, Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia, and bInstituto de Física de São Carlos, IFSC, Universidade de São Paulo, USP, São Carlos, SP, Brazil
Correspondence e-mail: rodimo26@yahoo.es

In the title compound, C18H15N3O2, the benzofuran ring system is essentially planar, the rings making a dihedral angle of 0.57 (9)°. The phenyl, furan and benzene rings subtend dihedral angles of 47.07 (10), 85.76 (7) and 86.04 (7)°, respectively, with the pyrazole ring. In the crystal, molecules are linked by weak N-H...N, N-H...O and C-H...O interactions, generating edge-fused R44(20), and R12(7) rings linked into sheets which are parallel to (010).

Related literature

For biological and pharmacological properties of benzofuranones, see: Yoganathan et al. (2003[Yoganathan, K., Rossant, C., Ng, S., Huang, Y., Butler, M. S. & Buss, A. D. (2003). J. Nat. Prod. 66, 1116-1117.]); Shode et al. (2002[Shode, F. O., Mahomed, A. S. & Rogers, C. B. (2002). Phytochemistry, 61, 955-957.]); Anderson et al. (2005[Anderson, J. T., Ting, A. E., Boozer, S., Brunden, K. R., Crumrine, C., Danzig, J., Dent, T., Faga, L., Harrington, J. J., Hodnick, W. F., Murphy, S. M., Pawlowski, G., Perry, R., Raber, A., Rundlett, S. E., Stricker-Krongrad, A., Wang, J. & Bennani, Y. L. (2005). J. Med. Chem. 48, 7096-7098.]); Puder et al. (2000[Puder, C., Zeeck, A. & Beil, W. J. (2000). J. Antibiot. 53, 329-336.]); Nannei et al. (2006[Nannei, R., Dallavalle, S., Merlini, L., Bava, A. & Nasini, G. (2006). J. Org. Chem. 71, 6277-6280.]); Brady et al. (2000[Brady, S. F., Wagenaar, M. M., Singh, M. P., Janson, J. E. & Clardy, J. (2000). Org. Lett. 2, 4043-4046.]); Malpani et al. (2013[Malpani, Y., Achary, R., Kim, S. Y., Jeong, H. C., Kim, P., Han, S. B., Kim, M., Lee, C.-K., Kim, J. N. & Jung, Y.-S. (2013). Eur. J. Med. Chem. 62, 534-544.]). For the synthesis of diverse pyrazole derivatives, see: Abonia et al. (2010[Abonia, R., Castillo, J., Insuasty, B., Quiroga, J., Nogueras, M. & Cobo, J. (2010). Eur. J. Org. Chem. 33, 6454-6463.]); Insuasty et al. (2012[Insuasty, B., Chamizo, L., Muñoz, J., Tigreros, A., Quiroga, J., Abonia, R., Nogueras, M. & Cobo, J. (2012). Arch. Pharm. 345, 275-286.], 2013[Insuasty, H., Insuasty, B., Castro, E., Quiroga, J. & Abonia, R. (2013). Tetrahedron Lett. 54, 1722-1725.]). For hydrogen bonding, see: Nardelli (1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) and for hydrogen-bond graph-set motifs, see: Etter (1990[Etter, M. (1990). Acc. Chem. Res. 23, 120-126.]); 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
  • C18H15N3O2

  • Mr = 305.33

  • Monoclinic, P 21 /c

  • a = 10.0451 (2) Å

  • b = 15.0631 (5) Å

  • c = 12.2008 (4) Å

  • [beta] = 123.257 (2)°

  • V = 1543.75 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 295 K

  • 0.32 × 0.22 × 0.15 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 15125 measured reflections

  • 3449 independent reflections

  • 2264 reflections with I > 2[sigma](I)

  • Rint = 0.043

Refinement
  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.173

  • S = 1.03

  • 3449 reflections

  • 212 parameters

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

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O1i 0.86 2.38 3.131 (2) 146
N1-H1B...N3ii 0.86 2.27 3.116 (2) 169
C8-H8...N3ii 1.013 (19) 2.51 (2) 3.484 (2) 159.9 (15)
Symmetry codes: (i) [x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; 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.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2119 ).


Acknowledgements

RMF and RA are grateful to the Universidad del Valle, Colombia, for partial financial support. JCC acknowledges his doctoral fellowship granted by COLCIENCIAS.

References

Abonia, R., Castillo, J., Insuasty, B., Quiroga, J., Nogueras, M. & Cobo, J. (2010). Eur. J. Org. Chem. 33, 6454-6463.  [CrossRef]
Anderson, J. T., Ting, A. E., Boozer, S., Brunden, K. R., Crumrine, C., Danzig, J., Dent, T., Faga, L., Harrington, J. J., Hodnick, W. F., Murphy, S. M., Pawlowski, G., Perry, R., Raber, A., Rundlett, S. E., Stricker-Krongrad, A., Wang, J. & Bennani, Y. L. (2005). J. Med. Chem. 48, 7096-7098.  [CrossRef] [PubMed] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Brady, S. F., Wagenaar, M. M., Singh, M. P., Janson, J. E. & Clardy, J. (2000). Org. Lett. 2, 4043-4046.  [CrossRef] [PubMed] [ChemPort]
Etter, M. (1990). Acc. Chem. Res. 23, 120-126.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Insuasty, B., Chamizo, L., Muñoz, J., Tigreros, A., Quiroga, J., Abonia, R., Nogueras, M. & Cobo, J. (2012). Arch. Pharm. 345, 275-286.  [CrossRef] [ChemPort]
Insuasty, H., Insuasty, B., Castro, E., Quiroga, J. & Abonia, R. (2013). Tetrahedron Lett. 54, 1722-1725.  [CrossRef] [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Malpani, Y., Achary, R., Kim, S. Y., Jeong, H. C., Kim, P., Han, S. B., Kim, M., Lee, C.-K., Kim, J. N. & Jung, Y.-S. (2013). Eur. J. Med. Chem. 62, 534-544.  [CrossRef] [ChemPort] [PubMed]
Nannei, R., Dallavalle, S., Merlini, L., Bava, A. & Nasini, G. (2006). J. Org. Chem. 71, 6277-6280.  [CrossRef] [PubMed] [ChemPort]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [IUCr Journals]
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Puder, C., Zeeck, A. & Beil, W. J. (2000). J. Antibiot. 53, 329-336.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Shode, F. O., Mahomed, A. S. & Rogers, C. B. (2002). Phytochemistry, 61, 955-957.  [CrossRef] [PubMed] [ChemPort]
Yoganathan, K., Rossant, C., Ng, S., Huang, Y., Butler, M. S. & Buss, A. D. (2003). J. Nat. Prod. 66, 1116-1117.  [Web of Science] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1181-o1182   [ doi:10.1107/S1600536813017479 ]

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