2-(2-Chloro­phen­yl)-3-methyl-5,6-diphenyl-2,3-dihydro­pyrazine

Anuradha, N.; Chitra, S.; Thiruvalluvar, A.; Pandiarajan, K.; Butcher, R.J.; Jasinski, J.P.; Golen, J.A.

doi:10.1107/S1600536811036336

Volume 67
Part 10
Page o2598
October 2011

Received 3 September 2011
Accepted 6 September 2011
Online 14 September 2011

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R = 0.052
wR = 0.150
Data-to-parameter ratio = 16.0
Details

2-(2-Chlorophenyl)-3-methyl-5,6-diphenyl-2,3-dihydropyrazine

N. Anuradha,^a S. Chitra,^b A. Thiruvalluvar,^a ^* K. Pandiarajan,^c R. J. Butcher,^d J. P. Jasinski ^e and J. A. Golen ^e

^aPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India,^bDepartment of Chemistry, K.S.R. College of Engineering, Tiruchengode 637 215, Tamilnadu, India,^cDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamilnadu, India,^dDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and ^eDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
Correspondence e-mail: thiruvalluvar.a@gmail.com

In the title molecule, C₂₃H₁₉ClN₂, the heterocyclic ring adopts a screw-boat conformation, with all substituents equatorial. The benzene ring at position 2 makes dihedral angles of 77.88 (12) and 76.31 (12)° with the phenyl rings at positions 5 and 6, respectively. The dihedral angle between the phenyl rings at positions 5 and 6 is 70.05 (10)°. The Cl atom is disordered over two positions with occupancy factors of 0.946 (5) and 0.054 (5). In the crystal, C-H [pi] interactions are found.

Related literature

For the biological properties of heterocyclic ring systems having a dihydropyrazine nucleus, see: Sondhi et al. (2005). For the use of dihydropyrazines, with reference to DNA breakage activity, see: Takechi et al. (2011). For the inhibition of the growth of Escherichia coli, see: Takeda et al. (2005). For a closely related crystal structure, see: Anuradha et al. (2009).

Experimental

Crystal data

C₂₃H₁₉ClN₂
M_r = 358.85
Monoclinic, P 2₁ /c
a = 10.5675 (8) Å
b = 19.7014 (9) Å
c = 10.4207 (7) Å
= 118.479 (9)°
V = 1907.0 (3) Å³
Z = 4
Cu K radiation
= 1.82 mm^-1
T = 298 K
0.25 × 0.14 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO, CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.659, T_max = 1.000
22812 measured reflections
3831 independent reflections
3092 reflections with I > 2(I)
R_int = 0.052

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.150
S = 1.04
3831 reflections
240 parameters
2 restraints
H-atom parameters constrained
_max = 0.32 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2, Cg3 and Cg4 are the centroids of the C21-C26, C51-C56 and C61-C66 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C24-H24Cg4ⁱ	0.93	2.80	3.643 (3)	152
C53-H53Cg2ⁱⁱ	0.93	2.99	3.873 (4)	159
C64-H64Cg3ⁱⁱⁱ	0.93	2.88	3.729 (2)	153
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y, -z; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO, CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO, CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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: WN2451 ).

Acknowledgements

JPJ acknowledges the NSF-MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

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.
Oxford Diffraction (2010). CrysAlis PRO, CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sondhi, S. M., Singh, N., Rajvanshi, S., Johar, M., Shukla, R., Raghubir, R. & Dastidar, S. G. (2005). Indian J. Chem. Sect. B, 44, 387-399.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Takechi, S., Kashige, N., Ishida, T. & Yamaguchi, T. (2011). J. Basic Appl. Chem. 1, 1-7.
Takeda, O., Takechi, S., Katoh, T. & Yamaguchi, T. (2005). Biol. Pharm. Bull. 28, 1161-1164.

organic compounds