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Volume 69 
Part 5 
Page o801  
May 2013  

Received 18 April 2013
Accepted 23 April 2013
Online 27 April 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.003 Å
R = 0.051
wR = 0.115
Data-to-parameter ratio = 15.1
Details
Open access

7-Methyl-1-phenyl-1,10-dihydropyrazolo[3,4-a]carbazole

aPostgraduate Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India,bDepartment of Chemistry, Tamkang University, Tamsui 25137, Taiwan,cDepartment of Chemistry, Bharathiar University, Coimbatore 641 046, Tamilnadu, India,dDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA,eSchool of Studies in Chemistry, Jiwaji University, Gwalior 474 011, MP, India, and fFaculty of Sciences, Department of Physics, Erciyes University, 38039 Kayseri, Turkey
Correspondence e-mail: thiruvalluvar.a@gmail.com

In the title molecule, C20H15N3, the atoms in the carbazole unit deviate from planarity [maximum deviation from mean plane = 0.1082 (15) Å]. The pyrrole ring makes dihedral angles of 3.17 (8)/4.10 (9), 7.20 (9) and 44.62 (9)° with the fused benzene, pyrazole and phenyl rings, respectively. In the crystal, molecules are linked via N-H...N hydrogen bonds, forming an infinite chain along [010]. Molecules are further linked by nine [pi]-[pi] [centroid-centroid distances vary from 3.6864 (11) to 3.9802 (11) Å] and one C-H...[pi] interaction, forming a three-dimensional network.

Related literature

For related structures and the biological and pharmacological activity of carbazole alkaloids, see: Archana et al. (2010[Archana, R., Prabakaran, K., Rajendra Prasad, K. J., Thiruvalluvar, A. & Butcher, R. J. (2010). Acta Cryst. E66, o3146.], 2011[Archana, R., Yamuna, E., Rajendra Prasad, K. J., Thiruvalluvar, A. & Butcher, R. J. (2011). Acta Cryst. E67, o1799.]).

[Scheme 1]

Experimental

Crystal data
  • C20H15N3

  • Mr = 297.35

  • Monoclinic, P 21 /c

  • a = 12.0727 (6) Å

  • b = 7.5934 (3) Å

  • c = 16.8355 (8) Å

  • [beta] = 104.087 (5)°

  • V = 1496.95 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 123 K

  • 0.43 × 0.35 × 0.30 mm

Data collection
  • Agilent Xcalibur Ruby Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.967, Tmax = 0.977

  • 6773 measured reflections

  • 3212 independent reflections

  • 2354 reflections with I > 2[sigma](I)

  • Rint = 0.032

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

  • wR(F2) = 0.115

  • S = 1.03

  • 3212 reflections

  • 213 parameters

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

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the N10/C10A/C5A/C5B/C9A pyrrole ring.

D-H...A D-H H...A D...A D-H...A
N10-H10...N2i 0.89 (2) 2.24 (2) 3.092 (2) 159 (2)
C17-H17B...Cg2ii 0.98 2.70 3.401 (2) 129
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+1, -y+2, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); 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: 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 PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97 and PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2506 ).


Acknowledgements

RJB acknowledges the NSF-MRI program (grant No. CHE0619278) for funds to purchase the X-ray diffractometer. SKG wishes to acknowledge the USIEF for the award of a Fulbright-Nehru Senior Research Fellowship.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Archana, R., Prabakaran, K., Rajendra Prasad, K. J., Thiruvalluvar, A. & Butcher, R. J. (2010). Acta Cryst. E66, o3146.  [CSD] [CrossRef] [details]
Archana, R., Yamuna, E., Rajendra Prasad, K. J., Thiruvalluvar, A. & Butcher, R. J. (2011). Acta Cryst. E67, o1799.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o801  [ doi:10.1107/S1600536813010994 ]

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