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Volume 69 
Part 6 
Page o828  
June 2013  

Received 15 March 2013
Accepted 29 April 2013
Online 4 May 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.051
wR = 0.117
Data-to-parameter ratio = 18.1
Details
Open access

9-[3-(Carbazol-9-yl)-5-methylphenyl]carbazole

aDepartment of Chemistry, Konyang University, Nonsan 320-711, Republic of Korea
Correspondence e-mail: jylee@konyang.ac.kr, jylee@konyang.ac.kr

The title compound, C31H22N2, crystallizes with two symmetry-independent molecules in the asymmetric unit. The molecules have slightly different conformations, the dihedral angles between the central phenyl ring and the carbazolyl groups being 56.29 (4) and 59.57 (4)° in one molecule and 48.71 (4) and 65.47 (4)° in the other. In the crystal, molecules are linked by weak C-H...[pi] and [pi]-[pi] [centroid-centroid distances = 3.7698 (10), 3.8292 (9), 3.9429 (10) and 3.9431 (10) Å].

Related literature

For the preparation of the title compound, see: Kwon et al. (2007[Kwon, T.-H., Kim, M. K., Kwon, J., Shin, D.-Y., Park, S. J., Lee, C.-L., Kim, J.-J. & Hong, J.-I. (2007). Chem. Mater. 19, 3673-3680.]). For the structure of the related compound 1,3-bis(carbazol-9-yl)benzene, see: Sun et al. (2006[Sun, Y.-H., Zhu, X.-H., Chen, Z., Zhang, Y. & Cao, Y. (2006). J. Org. Chem. 71, 6281-6284.]).

[Scheme 1]

Experimental

Crystal data
  • C31H22N2

  • Mr = 422.51

  • Monoclinic, P 21 /n

  • a = 9.2503 (1) Å

  • b = 29.3854 (4) Å

  • c = 16.2616 (2) Å

  • [beta] = 96.901 (1)°

  • V = 4388.27 (9) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 173 K

  • 0.26 × 0.23 × 0.22 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.981, Tmax = 0.984

  • 42985 measured reflections

  • 10834 independent reflections

  • 7284 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.117

  • S = 1.03

  • 10834 reflections

  • 598 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
C-H...[pi] (Å, °)

Cg1, Cg3-Cg6 and Cg9 are the centroids of the C44-C49, C7-C12, C56-C61, C1-C6, C19-C24 and C32-C37 benzene rings while Cg2, Cg7 and Cg8 are the centroids of the N4/C50/C55/C56/C61, N2/C19/C24/C25/C30 and N3/C32/C37/C38/C43 pyrrole rings.

C-H...[pi] C-H H...Cg C...Cg C-H...Cg
C9-H9A...Cg1i 0.95 2.96 3.776 (2) 145
C5-H5A...Cg2ii 0.95 2.77 3.6969 (19) 165
C53-H53A...Cg3iii 0.95 2.76 3.5983 (19) 148
C8-H8A...Cg4ii 0.95 2.81 3.7122 (19) 160
C49-H49A...Cg5 0.95 2.98 3.8654 (16) 156
C57-H57A...Cg6iv 0.95 2.85 3.3776 (17) 117
C58-H58A...Cg7iv 0.95 2.88 3.3749 (18) 114
C59-H59A...Cg8v 0.95 2.66 3.5084 (18) 149
C60-H60A...Cg9v 0.95 2.74 3.5180 (17) 140
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iii) x, y, z-1; (iv) -x, -y+1, -z+1; (v) x-1, y, z.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2006[Bruker (2006). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2283 ).


Acknowledgements

This paper was supported by the Konyang University Research Fund in 2012 and also the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2011-0007756). The authors gratefully acknowledge the use of the SC-XRD in the Korea Basic Science Institute (Jeonju Center).

References

Bruker (2006). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Kwon, T.-H., Kim, M. K., Kwon, J., Shin, D.-Y., Park, S. J., Lee, C.-L., Kim, J.-J. & Hong, J.-I. (2007). Chem. Mater. 19, 3673-3680.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Sun, Y.-H., Zhu, X.-H., Chen, Z., Zhang, Y. & Cao, Y. (2006). J. Org. Chem. 71, 6281-6284.  [CSD] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o828  [ doi:10.1107/S1600536813011641 ]

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