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Volume 70 
Part 1 
Page o28  
January 2014  

Received 27 November 2013
Accepted 2 December 2013
Online 7 December 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.001 Å
R = 0.040
wR = 0.068
Data-to-parameter ratio = 15.8
Details
Open access

1-Nitro-9H-carbazole

aInstitute for Applied Synthetic Chemistry, Division Organic Chemistry, Vienna University of Technology, Getreidemarkt 9/163-OC, A-1060 Vienna, Austria, and bInstitute for Chemical Technologies and Analytics, Division Structural Chemistry, Vienna University of Technology, Getreidemarkt 9/164-SC, A-1060 Vienna, Austria
Correspondence e-mail: bstoeger@mail.tuwien.ac.at

In the title mol­ecule, C12H8N2O2, the nitro group is tilted slightly with respect to the carbazole moiety [angle between the least-squares planes = 4.43 (9)°]. In the crystal, the mol­ecules are connected via pairs of N-H...O hydrogen bonds into dimers with -1 symmetry. The dimers in turn are arranged into layers parallel to (10-1).

Related literature

For the applications of aryl­amines as electron donors, see: Shirota & Kageyama (2007[Shirota, Y. & Kageyama, H. (2007). Chem. Rev. 107, 953-1010.]); Tao et al. (2011[Tao, Y., Yang, C. & Qin, J. (2011). Chem. Soc. Rev. 40, 2943-2970.]); Yook & Lee (2012[Yook, K. S. & Lee, J. Y. (2012). Adv. Mater. 24, 3169-3190.]); Kautny et al. (2014[Kautny, P., Lumpi, D., Wang, Y., Tissot, A., Bintinger, J., Horkel, E., Stöger, B., Hametner, C., Hageman, H.-R., Ma, D. & Fröhlich, J. (2014). Mater. Chem. C Submitted.]). For the synthesis of the catalyst (NHC)Pd(all­yl)Cl, see: Marion et al. (2006[Marion, N., Navarro, O., Mei, J., Stevens, E. D., Scott, N. M. & Nolan, S. P. (2006). J. Am. Chem. Soc. 95, 4101-4111.]).

[Scheme 1]

Experimental

Crystal data
  • C12H8N2O2

  • Mr = 212.2

  • Monoclinic, P 21 /n

  • a = 10.4400 (3) Å

  • b = 5.3148 (2) Å

  • c = 17.2638 (6) Å

  • [beta] = 99.7460 (16)°

  • V = 944.08 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 100 K

  • 0.76 × 0.42 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). SAINT-Plus, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.95, Tmax = 0.98

  • 30130 measured reflections

  • 2794 independent reflections

  • 2397 reflections with I > 3[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 3[sigma](F2)] = 0.040

  • wR(F2) = 0.068

  • S = 1.89

  • 2794 reflections

  • 177 parameters

  • All H-atom parameters refined

  • [Delta][rho]max = 0.32 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
N1-Hn1...O1i 0.857 (13) 2.159 (13) 2.9940 (10) 164.6 (14)
Symmetry code: (i) -x+2, -y+1, -z.

Data collection: APEX2 (Bruker, 2013[Bruker (2013). SAINT-Plus, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2013[Bruker (2013). SAINT-Plus, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: JANA2006 (Petrícek et al., 2006[Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic.]); molecular graphics: ATOMS (Dowty, 2006[Dowty, E. (2006). ATOMS. Shape Software, Kingsport, Tennessee, USA.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2123 ).


Acknowledgements

The X-ray centre (XRC) of the Vienna University of Technology is acknowledged for providing access to the single-crystal diffractometer and for financial support.

References

Bruker (2013). SAINT-Plus, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dowty, E. (2006). ATOMS. Shape Software, Kingsport, Tennessee, USA.
Kautny, P., Lumpi, D., Wang, Y., Tissot, A., Bintinger, J., Horkel, E., Stöger, B., Hametner, C., Hageman, H.-R., Ma, D. & Fröhlich, J. (2014). Mater. Chem. C Submitted.
Marion, N., Navarro, O., Mei, J., Stevens, E. D., Scott, N. M. & Nolan, S. P. (2006). J. Am. Chem. Soc. 95, 4101-4111.  [Web of Science] [CSD] [CrossRef]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic.
Shirota, Y. & Kageyama, H. (2007). Chem. Rev. 107, 953-1010.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Tao, Y., Yang, C. & Qin, J. (2011). Chem. Soc. Rev. 40, 2943-2970.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Yook, K. S. & Lee, J. Y. (2012). Adv. Mater. 24, 3169-3190.  [Web of Science] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2014). E70, o28  [ doi:10.1107/S1600536813032704 ]

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