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

Thiruvalluvar, A.; Anuradha, N.; Chitra, S.; Devanathan, D.; Butcher, R.J.

doi:10.1107/S1600536812041438

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 (C-C) = 0.003 Å
Disorder in main residue
R = 0.069
wR = 0.214
Data-to-parameter ratio = 15.3
Details

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

A. Thiruvalluvar,^a ^* N. Anuradha,^a S. Chitra,^b D. Devanathan ^c and R. J. Butcher ^d

^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, 2011).

Experimental

Crystal data

C₂₄H₂₂N₂
M_r = 338.44
Monoclinic, P 2₁ /c
a = 8.1986 (5) Å
b = 11.8211 (6) Å
c = 19.6686 (7) Å
= 93.638 (4)°
V = 1902.38 (17) Å³
Z = 4
Cu K radiation
= 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) T_min = 0.830, T_max = 1.000
12585 measured reflections
3892 independent reflections
3044 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.069
wR(F²) = 0.214
S = 1.07
3892 reflections
254 parameters
68 restraints
H-atom parameters constrained
_max = 0.71 e Å^-3
_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-HA	D-H	HA	DA	D-HA
C10-H10ACg4ⁱ	0.95	2.95	3.743 (3)	142
C19-H19ACg4ⁱⁱ	0.95	2.77	3.578 (3)	143
C22-H22ACg3ⁱⁱⁱ	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

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.
Anuradha, N., Thiruvalluvar, A., Pandiarajan, K., Chitra, S. & Butcher, R. J. (2009). Acta Cryst. E65, o546.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds