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Volume 69 
Part 12 
Pages o1826-o1827  
December 2013  

Received 5 November 2013
Accepted 20 November 2013
Online 27 November 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.053
wR = 0.172
Data-to-parameter ratio = 20.7
Details
Open access

5-[(tert-Butyl­diphenyl­sil­yloxy)meth­yl]pyridazin-3(2H)-one

aDepartment of Organic Chemistry, University of Vigo, E-36310 Vigo, Spain
Correspondence e-mail: mcteran@uvigo.es

In the title compound, C21H24N2O2Si, a new pyridazin-3(2H)-one derivative, the carbonyl group of the heterocyclic ring and the O atom of the silyl ether are located on the same side of the pyridazinone ring and the C-C-O-Si torsion angle is -140.69 (17)°. In the crystal, mol­ecules are linked by pairs of strong N-H...O hydrogen bonds into centrosymmetric dimers with graph-set notation R22(8). Weak C-H...[pi] inter­actions are also observed.

Related literature

For background to related compounds displaying biological activity, see: Siddiqui et al. (2010[Siddiqui, A. A., Mishra, R. & Shaharyar, M. (2010). Eur. J. Med. Chem. 45, 2283-2290.]); Moos et al. (1987[Moos, W. H., Humblet, C. C., Sircar, I., Rithner, C., Weishaar, R. E., Bristol, J. A. & McPhail, A. T. (1987). J. Med. Chem. 30, 1963-1972.]); Coelho et al. (2007[Coelho, A., Raviña, E., Fraiz, N., Yañez, M., Laguna, R., Cano, E. & Sotelo, E. (2007). J. Med. Chem. 50, 6476-6484.]); Abouzid & Bekhit (2008[Abouzid, K. & Bekhit, S. A. (2008). Bioorg. Med. Chem. 16, 5547-5556.]); Cesari et al. (2006[Cesari, N., Biancanali, C., Vergelli, C., Dal Piaz, V., Graziano, A., Biagini, P., Chelardini, C., Galeotti, N. & Giovannoni, P. (2006). J. Med. Chem. 49, 7826-7835.]); Rathish et al. (2009[Rathish, I. G., Javed, K., Bano, S., Ahmad, S., Alam, M. S. & Pillai, K. K. (2009). Eur. J. Med. Chem. 44, 2673-2678.]); Sivakumar et al. (2003[Sivakumar, R., Anabalagan, N., Gunasekaran, V. & Leonard, J. T. (2003). Biol. Pharm. Bull. 26, 1407-1411.]); Al-Tel (2010[Al-Tel, T. H. (2010). Eur. J. Med. Chem. 45, 5724-5731.]); Suree et al. (2009[Suree, N., Yi, S. W., Thieu, W., Marohn, M., Damoiseaux, R., Chan, A., Jung, M. E. & Club, R. T. (2009). Bioorg. Med. Chem. 17, 7174-7185.]); Tao et al. (2011[Tao, M., Raddatz, R., Aimone, L. D. & Hudkins, R. L. (2011). Bioorg. Med. Chem. Lett. 21, 6126-6130.]); Weishaar et al. (1985[Weishaar, R. W., Cain, M. H. & Bristol, J. A. (1985). J. Med. Chem. 28, 537-545.]). For related structures, see: Costas et al. (2010[Costas, T., Besada, P., Piras, A., Acevedo, L., Yañez, M., Orallo, F., Laguna, R. & Terán, C. (2010). Bioorg. Med. Chem. Lett. 20, 6624-6627.]). 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.]).

[Scheme 1]

Experimental

Crystal data
  • C21H24N2O2Si

  • Mr = 364.51

  • Monoclinic, P 21 /c

  • a = 7.9844 (10) Å

  • b = 14.1416 (17) Å

  • c = 18.553 (2) Å

  • [beta] = 98.158 (2)°

  • V = 2073.6 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 293 K

  • 0.49 × 0.47 × 0.35 mm

Data collection
  • Bruker SMART 1000 CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.704, Tmax = 0.746

  • 25441 measured reflections

  • 5012 independent reflections

  • 3090 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.172

  • S = 1.01

  • 5012 reflections

  • 242 parameters

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

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C8'-C13' ring.

D-H...A D-H H...A D...A D-H...A
N2-H2...O3i 0.89 (3) 1.93 (3) 2.812 (2) 173 (2)
C6-H6...Cg3ii 0.93 3.00 3.869 (3) 157
Symmetry codes: (i) -x+1, -y, -z; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madinson, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madinson, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]) 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2453 ).


Acknowledgements

This work was supported financially by the Xunta de Galicia (CN 2012/184). The authors gratefully acknowledge Dr Berta Covelo, X-ray Diffraction service of the University of Vigo, for her valuable assistance. MCC-L and NV thank the University of Vigo for their Master and PhD fellowships, respectively.

References

Abouzid, K. & Bekhit, S. A. (2008). Bioorg. Med. Chem. 16, 5547-5556.  [CrossRef] [PubMed] [ChemPort]
Al-Tel, T. H. (2010). Eur. J. Med. Chem. 45, 5724-5731.  [Web of Science] [ChemPort] [PubMed]
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 (1998). SMART and SAINT. Bruker AXS Inc., Madinson, Wisconsin, USA.
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Cesari, N., Biancanali, C., Vergelli, C., Dal Piaz, V., Graziano, A., Biagini, P., Chelardini, C., Galeotti, N. & Giovannoni, P. (2006). J. Med. Chem. 49, 7826-7835.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Coelho, A., Raviña, E., Fraiz, N., Yañez, M., Laguna, R., Cano, E. & Sotelo, E. (2007). J. Med. Chem. 50, 6476-6484.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Costas, T., Besada, P., Piras, A., Acevedo, L., Yañez, M., Orallo, F., Laguna, R. & Terán, C. (2010). Bioorg. Med. Chem. Lett. 20, 6624-6627.  [CrossRef] [ChemPort] [PubMed]
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]
Moos, W. H., Humblet, C. C., Sircar, I., Rithner, C., Weishaar, R. E., Bristol, J. A. & McPhail, A. T. (1987). J. Med. Chem. 30, 1963-1972.  [CSD] [CrossRef] [ChemPort] [PubMed] [Web of Science]
Rathish, I. G., Javed, K., Bano, S., Ahmad, S., Alam, M. S. & Pillai, K. K. (2009). Eur. J. Med. Chem. 44, 2673-2678.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Siddiqui, A. A., Mishra, R. & Shaharyar, M. (2010). Eur. J. Med. Chem. 45, 2283-2290.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Sivakumar, R., Anabalagan, N., Gunasekaran, V. & Leonard, J. T. (2003). Biol. Pharm. Bull. 26, 1407-1411.  [CrossRef] [PubMed] [ChemPort]
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Suree, N., Yi, S. W., Thieu, W., Marohn, M., Damoiseaux, R., Chan, A., Jung, M. E. & Club, R. T. (2009). Bioorg. Med. Chem. 17, 7174-7185.  [CrossRef] [PubMed] [ChemPort]
Tao, M., Raddatz, R., Aimone, L. D. & Hudkins, R. L. (2011). Bioorg. Med. Chem. Lett. 21, 6126-6130.  [CrossRef] [ChemPort] [PubMed]
Weishaar, R. W., Cain, M. H. & Bristol, J. A. (1985). J. Med. Chem. 28, 537-545.  [CrossRef] [ChemPort] [PubMed] [Web of Science]


Acta Cryst (2013). E69, o1826-o1827   [ doi:10.1107/S160053681303167X ]

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