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Volume 69 
Part 10 
Page o1499  
October 2013  

Received 21 August 2013
Accepted 28 August 2013
Online 4 September 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.002 Å
R = 0.036
wR = 0.098
Data-to-parameter ratio = 11.8
Details
Open access

1-(4-{[(1,3,3-Trimethylindolin-2-ylidene)methyl]diazenyl}phenyl)ethanone

The title compound, C20H21N3O, has crystallographic mirror symmetry with all non-H atoms apart from the methyl C atom of the CMe2 group lying on the mirror plane. Molecules are linked into planar sheets parallel to (010) by phenyl-azo C-H...N and phenyl-ethanone C-H...O interactions. Methyl C-H...[pi] interactions provide crosslinking between the planes.

Related literature

For general background to NLO chromophores, see: Dalton et al. (2011[Dalton, L. R., Benight, S. J., Johnson, L. E., Knorr, D. B., Kosilkin, I. & Eichinger, B. E. (2011). Chem. Mater. 23, 430-445.]); Marder et al. (1994[Marder, S. R., Cheng, L. T., Tiemann, B. G., Friedli, A. C., Blanchard, D. M. & Perry, J. W. (1994). Science, 263, 511-514.]); Cheng et al. (1991[Cheng, L. T., Tam, W., Stevenson, S. H., Meredith, G. R., Rikken, G. & Marder, S. R. (1991). J. Phys. Chem. 95, 10631-10643.]); Mashraqui et al. (2004[Mashraqui, S. H., Kenny, R. S., Ghadigaonkar, S. G., Krishnan, A., Bhattacharya, M. & Das, P. K. (2004). Opt. Mater. 27, 257-260.]); Moylan et al. (1993[Moylan, C. R., Twieg, R. J., Lee, V. Y., Swanson, S. A., Betterton, K. M. & Miller, R. D. (1993). J. Am. Chem. Soc. 115, 12599-12600.]); Zhang et al. (1997[Zhang, J. X., Dubois, P. & Jerome, R. J. (1997). J. Chem. Soc. Perkin Trans. 2, pp. 1209-1216.]); Prim et al. (1994[Prim, D. & Krisch, G. (1994). J. Chem. Soc. Perkin Trans. 1, pp. 2603-2606.]). For related structures, see: Odabasoglu et al. (2005[Odabasoglu, M., Turgut, G., Karadayi, N. & Buyukgungor, O. (2005). Dyes Pigm. 64, 271-278.]); Simunek et al. (2003[Simunek, P., Bertolasi, V., Lycka, A. & Machacek, V. (2003). Org. Biomol. Chem. 1, 3250-3256.]); Bhuiyan et al. (2011[Bhuiyan, M. D. H., Ashraf, M., Teshome, A., Gainsford, G. J., Kay, A. J., Asselberghs, I. & Clays, K. (2011). Dyes Pigm. 89, 177-187.]); Ashraf et al. (2013[Ashraf, M., Teshome, A., Kay, A. J., Gainsford, G. J., Bhuiyan, M. D. H., Asselberghs, I. & Clays, K. (2013). Dyes Pigm. 98, 82-92.]). For analysis of the structures, see: Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C20H21N3O

  • Mr = 319.40

  • Monoclinic, C 2/m

  • a = 14.8688 (2) Å

  • b = 6.89500 (12) Å

  • c = 16.3546 (3) Å

  • [beta] = 99.5834 (16)°

  • V = 1653.27 (5) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.64 mm-1

  • T = 120 K

  • 0.19 × 0.15 × 0.09 mm

Data collection
  • Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

  • Absorption correction: gaussian (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies, Santa Clara, CA, USA.]) Tmin = 0.804, Tmax = 1.000

  • 9379 measured reflections

  • 1803 independent reflections

  • 1634 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.098

  • S = 1.07

  • 1803 reflections

  • 153 parameters

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

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...O1i 0.95 2.57 3.5227 (19) 179
C14-H14...N3ii 0.95 2.55 3.4985 (19) 175
C11-H11A...Cg3iii 0.981 (15) 2.665 (14) 3.5230 (4) 145.8 (11)
Symmetry codes: (i) x-1, y, z; (ii) -x+1, y, -z; (iii) -x-1, -y, -z.

Data collection: CrysAlis PRO (Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies, Santa Clara, CA, USA.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2012[Sheldrick, G. M. (2012). SHELXL2012. University of Göttingen, Germany.]); 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: SHELXL2012, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and Mercury.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5249 ).


Acknowledgements

We thank Dr Matthew Colson of the University of Canterbury for the data collection.

References

Agilent (2013). CrysAlis PRO. Agilent Technologies, Santa Clara, CA, USA.
Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [Web of Science] [CrossRef] [IUCr Journals]
Ashraf, M., Teshome, A., Kay, A. J., Gainsford, G. J., Bhuiyan, M. D. H., Asselberghs, I. & Clays, K. (2013). Dyes Pigm. 98, 82-92.  [CrossRef] [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]
Bhuiyan, M. D. H., Ashraf, M., Teshome, A., Gainsford, G. J., Kay, A. J., Asselberghs, I. & Clays, K. (2011). Dyes Pigm. 89, 177-187.  [CrossRef] [ChemPort]
Cheng, L. T., Tam, W., Stevenson, S. H., Meredith, G. R., Rikken, G. & Marder, S. R. (1991). J. Phys. Chem. 95, 10631-10643.  [CrossRef] [ChemPort] [Web of Science]
Dalton, L. R., Benight, S. J., Johnson, L. E., Knorr, D. B., Kosilkin, I. & Eichinger, B. E. (2011). Chem. Mater. 23, 430-445.  [Web of Science] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
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]
Marder, S. R., Cheng, L. T., Tiemann, B. G., Friedli, A. C., Blanchard, D. M. & Perry, J. W. (1994). Science, 263, 511-514.  [CSD] [CrossRef] [PubMed] [ChemPort] [Web of Science]
Mashraqui, S. H., Kenny, R. S., Ghadigaonkar, S. G., Krishnan, A., Bhattacharya, M. & Das, P. K. (2004). Opt. Mater. 27, 257-260.  [Web of Science] [CrossRef] [ChemPort]
Moylan, C. R., Twieg, R. J., Lee, V. Y., Swanson, S. A., Betterton, K. M. & Miller, R. D. (1993). J. Am. Chem. Soc. 115, 12599-12600.  [CrossRef] [ChemPort] [Web of Science]
Odabasoglu, M., Turgut, G., Karadayi, N. & Buyukgungor, O. (2005). Dyes Pigm. 64, 271-278.  [ChemPort]
Prim, D. & Krisch, G. (1994). J. Chem. Soc. Perkin Trans. 1, pp. 2603-2606.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2012). SHELXL2012. University of Göttingen, Germany.
Simunek, P., Bertolasi, V., Lycka, A. & Machacek, V. (2003). Org. Biomol. Chem. 1, 3250-3256.  [PubMed] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Zhang, J. X., Dubois, P. & Jerome, R. J. (1997). J. Chem. Soc. Perkin Trans. 2, pp. 1209-1216.


Acta Cryst (2013). E69, o1499  [ doi:10.1107/S1600536813024124 ]

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