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Volume 68 
Part 11 
Page o3084  
November 2012  

Received 28 September 2012
Accepted 2 October 2012
Online 6 October 2012

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.069
wR = 0.214
Data-to-parameter ratio = 15.3
Details
Open access

2-Methyl-3-(4-methylphenyl)-5,6-diphenyl-2,3-dihydropyrazine

aPostgraduate Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India,bDepartment of Chemistry, KSR College of Engineering, KSR Kalvi Nagar, Tiruchengode 637 215, Tamilnadu, India,cDepartment of Chemistry, Government Arts College, C. Mutlur 608 102, Chidambaram, Tamilnadu, India, and dDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
Correspondence e-mail: thiruvalluvar.a@gmail.com

In the title molecule, C24H22N2, four atoms (N-C-C-N) of the heterocyclic ring, with their attached H atoms, and all atoms of the methyl group, are disordered over two positions; the site-occupancy factor of the major component is 0.713 (6). The major disorder component of the heterocyclic ring adopts a half-chair conformation, with all substituents equatorial. The benzene ring adjacent to the methyl group forms dihedral angles of 79.68 (11) and 80.92 (11)° with the phenyl rings; the dihedral angle between adjacent phenyl rings is 59.10 (11)°. The crystal structure features three C-H...[pi] interactions.

Related literature

For the biological properties of dihydropyrazines and for closely related crystal structures, see: Anuradha et al. (2009[Anuradha, N., Thiruvalluvar, A., Pandiarajan, K., Chitra, S. & Butcher, R. J. (2009). Acta Cryst. E65, o546.], 2011[Anuradha, N., Chitra, S., Thiruvalluvar, A., Pandiarajan, K., Butcher, R. J., Jasinski, J. P. & Golen, J. A. (2011). Acta Cryst. E67, o2598.]).

[Scheme 1]

Experimental

Crystal data
  • C24H22N2

  • Mr = 338.44

  • Monoclinic, P 21 /c

  • a = 8.1986 (5) Å

  • b = 11.8211 (6) Å

  • c = 19.6686 (7) Å

  • [beta] = 93.638 (4)°

  • V = 1902.38 (17) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.53 mm-1

  • T = 123 K

  • 0.39 × 0.21 × 0.17 mm

Data collection
  • Agilent Xcalibur Ruby Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.830, Tmax = 1.000

  • 12585 measured reflections

  • 3892 independent reflections

  • 3044 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.069

  • wR(F2) = 0.214

  • S = 1.07

  • 3892 reflections

  • 254 parameters

  • 68 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.71 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 and Cg4 are the centroids of the C6-C11 and C12-C17 phenyl rings, respectively.

D-H...A D-H H...A D...A D-H...A
C10-H10A...Cg4i 0.95 2.95 3.743 (3) 142
C19-H19A...Cg4ii 0.95 2.77 3.578 (3) 143
C22-H22A...Cg3iii 0.95 2.66 3.590 (3) 165
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y+2, -z; (iii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5255 ).


Acknowledgements

RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Anuradha, N., Chitra, S., Thiruvalluvar, A., Pandiarajan, K., Butcher, R. J., Jasinski, J. P. & Golen, J. A. (2011). Acta Cryst. E67, o2598.  [CSD] [CrossRef] [details]
Anuradha, N., Thiruvalluvar, A., Pandiarajan, K., Chitra, S. & Butcher, R. J. (2009). Acta Cryst. E65, o546.  [CSD] [CrossRef] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o3084  [ doi:10.1107/S1600536812041438 ]

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