N-[2-(3-Methyl-1-oxo-1,2-dihydro­pyrrolo­[1,2-a]pyrazin-2-yl)eth­yl]methane­sulfonamide

Khan, S.T.; Yu, P.; Chantrapromma, S.; Afza, N.; Nelofar, A.

doi:10.1107/S1600536810026115

Volume 66
Part 8
Page o1957
August 2010

Received 30 June 2010
Accepted 2 July 2010
Online 10 July 2010

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.002 Å
R = 0.040
wR = 0.105
Data-to-parameter ratio = 17.6
Details

N-[2-(3-Methyl-1-oxo-1,2-dihydropyrrolo[1,2-a]pyrazin-2-yl)ethyl]methanesulfonamide

Salman Tariq Khan,^a ^* Peng Yu,^b Suchada Chantrapromma,^c ⁺ Nighat Afza ^a and Aisha Nelofar ^a

^aPharmaceutical Research Centre, PCSIR Labs Complex, Karachi 75280, Pakistan,^bDepartment of Pharmaceutical Engineering, Biotechnology College, Tianjin University of Science & Technology (TUST), Tianjin 300457, People's Republic of China, and ^cCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
Correspondence e-mail: salmankhann@hotmail.com

In the title compound, C₁₁H₁₅N₃O₃S, the dihedral angle between the five- and six-membered rings is 1.13 (18)°. The ethylmethanesulfonamide group is in a (+)synclinal conformation. In the crystal, intermolecular N-HO and C-HO hydrogen-bond interactions link molecules into zigzag ribbons parallel to the b axis. The ribbons are further connected by C-H [pi] interactions.

Related literature

For the biological activity of pyrrolopyrazinone derivatives, see: Dubis et al. (1995); Micheli et al. (2008); Wang et al. (2004); Zöllinger et al. (2007). For standard bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₁H₁₅N₃O₃S
M_r = 269.33
Monoclinic, P 2₁ /c
a = 5.492 (1) Å
b = 20.631 (4) Å
c = 11.212 (2) Å
= 99.953 (6)°
V = 1251.3 (4) Å³
Z = 4
Mo K radiation
= 0.26 mm^-1
T = 113 K
0.18 × 0.12 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.954, T_max = 0.974
9267 measured reflections
2969 independent reflections
2499 reflections with I > 2(I)
R_int = 0.036

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.105
S = 1.05
2969 reflections
169 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.22 e Å^-3
_min = -0.46 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N2/C4-C7 ring.

D-HA	D-H	HA	DA	D-HA
N3-H1N3O1ⁱ	0.82 (2)	1.99 (2)	2.7923 (18)	168 (2)
C4-H4AO3ⁱⁱ	0.95	2.36	3.258 (2)	157
C8-H8ACg1ⁱⁱⁱ	0.99	2.96	3.5153 (19)	116
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) $[x-1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x+1, y, z.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2471 ).

Acknowledgements

STK thanks Dr Song Haibin of The State Key Laboratory of Elemento-Organic Chemistry, Nankai University, for the data collection. PY is grateful to Tianjin University of Science & Technology for a research grant (No. 2009 0431).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Dubis, E., Dubis, A., Nawrot, J., Winiecki, Z. & Poplawski, J. (1995). Proceedings of the 1st International Conference on Insects, Insects-Chemical, Physiological and Environmental Aspects, Ládek-Zdrój, University of Wroclaw, Poland.
Micheli, F., Bertani, B., Bozzoli, A., Crippa, L., Cavanni, P., Di Fabio, R., Donati, D., Marzorati, P., Merlo, G., Paio, A., Perugini, L. & Zarantonello, P. (2008). Bioorg. Med. Chem. Lett. 18, 1804-1809.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wang, F., Wang, J. & Zhang, S. (2004). Molecules, 9, 574-582.
Zöllinger, M., Kelter, G., Fiebig, H.-H. & Lindel, T. (2007). Bioorg. Med. Chem. Lett. 17, 346-349.

organic compounds