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

organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o1957

https://doi.org/10.1107/S1600536810026115

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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

(Received 30 June 2010; accepted 2 July 2010; online 10 July 2010)

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—H⋯O and C—H⋯O hydrogen-bond interactions link molecules into zigzag ribbons parallel to the b axis. The ribbons are further connected by C—H⋯π 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
β = 99.953 (6)°
V = 1251.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(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
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯O1ⁱ	0.82 (2)	1.99 (2)	2.7923 (18)	168 (2)
C4—H4A⋯O3ⁱⁱ	0.95	2.36	3.258 (2)	157
C8—H8A⋯Cg1ⁱⁱⁱ	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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810026115/rz2471sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810026115/rz2471Isup2.hkl

checkCIF report

Comment top

Pyrrolopyrazinone compounds have been found to possess antitumor activity (Zöllinger et al., 2007), antifeedant effect on storage pests (Dubis et al., 1995) and to be potent and selective non-competitive mGluR5 antagonists (Micheli et al., 2008). Due to the interesting biological activities of pyrrolopyrazinone compounds, the title compound, which may have an improved analgesic activity (Wang et al., 2004), was synthesized and its crystal structure is reported here.

In the title compound (Fig. 1), the nine non-hydrogen atoms of the pyrrolopyrazine ring system are nearly coplanar (r.m.s. deviation 0.0107 (2) Å) and the dihedral angle between the five and six membered rings is 1.13 (18)°. The ethylmethanesulfonamide group (C8–C10/N3/S1/O2–O3) is in (+)-synclinal conformation, as indicated by the C1–N1–C8–C9 torsion angle of 83.75 (16)°. The dihedral angle between the mean planes through C8/C9/C10 and N3/C9/S1 is 79.58 (19)°. The bond lengths are in normal ranges (Allen et al., 1997). In the crystal structure (Fig. 2), centrosymmetrically related molecules are linked by N—H···O hydrogen bonds (Table 1) into dimers forming fourteen-membered rings with R₂²(14) motifs (Bernstein et al., 1995). Adjacent dimers are linked by C—H···O hydrogen interactions into zigzag ribbons running parallel to the b axis. The crystal packing is further stabilized by inter-ribbon C—H···π interactions (Table 1; Cg1 is the centroid of the N2/C4–C7 ring).

Related literature top

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 top

The title compound was prepared by reacting 2-(2-aminoethyl)-3-hydroxy-3-methyl-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one (2.39 mmol) and methanesulfonyl chloride (4.76 mmol) in pyridine (2 ml) for 4 h. The reaction mixture was then poured into ice cold water and the solid obtained was filtered and washed thoroughly with water and then dissolved in aqueous NaHCO₃ solution. Filtration and then the acidification with dilute HCl gave the title compound as precipitate, which was then filtered and dried. Colourless block-shaped single crystals of the title compound suitable for X-ray structure determination were recrystalized from a dichloromethane/methanol solution (9.5:0.5 v/v) on slow evaporation of the solvent at room temperature after several days.

Structure description top

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).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound viewed along the a axis. Hydrogen bonds are drawn as dashed lines.

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

Crystal data top

C₁₁H₁₅N₃O₃S	F(000) = 568
M_r = 269.33	D_x = 1.430 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2969 reflections
a = 5.492 (1) Å	θ = 2.0–27.9°
b = 20.631 (4) Å	µ = 0.26 mm⁻¹
c = 11.212 (2) Å	T = 113 K
β = 99.953 (6)°	Block, colourless
V = 1251.3 (4) Å³	0.18 × 0.12 × 0.10 mm
Z = 4

Data collection top

Rigaku Saturn CCD area-detector diffractometer	2969 independent reflections
Radiation source: rotating anode	2499 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.036
Detector resolution: 14.63 pixels mm^-1	θ_max = 27.9°, θ_min = 2.0°
ω and φ scans	h = −6→7
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −27→26
T_min = 0.954, T_max = 0.974	l = −14→14
9267 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.058P)² + 0.0584P] where P = (F_o² + 2F_c²)/3
2969 reflections	(Δ/σ)_max = 0.001
169 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₁₁H₁₅N₃O₃S	V = 1251.3 (4) Å³
M_r = 269.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.492 (1) Å	µ = 0.26 mm⁻¹
b = 20.631 (4) Å	T = 113 K
c = 11.212 (2) Å	0.18 × 0.12 × 0.10 mm
β = 99.953 (6)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.22 e Å⁻³
2969 reflections	Δρ_min = −0.46 e Å⁻³
169 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.99680 (7)	0.594929 (18)	0.15089 (3)	0.02298 (13)
O1	0.7267 (2)	0.54127 (5)	0.61880 (10)	0.0287 (3)
O2	1.2319 (2)	0.57634 (7)	0.12187 (11)	0.0358 (3)
O3	0.9462 (2)	0.66268 (6)	0.16584 (12)	0.0391 (3)
N1	0.7215 (2)	0.63970 (6)	0.52476 (11)	0.0204 (3)
N2	0.3756 (2)	0.68495 (6)	0.65521 (11)	0.0210 (3)
N3	0.9639 (3)	0.55700 (7)	0.27108 (13)	0.0291 (3)
H1N3	1.063 (4)	0.5283 (10)	0.2942 (19)	0.042 (6)*
C1	0.6456 (3)	0.59733 (7)	0.60737 (14)	0.0212 (3)
C2	0.6279 (3)	0.70370 (7)	0.50739 (14)	0.0211 (3)
C3	0.4595 (3)	0.72539 (7)	0.57091 (13)	0.0222 (3)
H3A	0.3970	0.7683	0.5587	0.027*
C4	0.2052 (3)	0.69648 (8)	0.72848 (15)	0.0273 (4)
H4A	0.1137	0.7353	0.7318	0.033*
C5	0.1905 (3)	0.64143 (8)	0.79670 (15)	0.0305 (4)
H5A	0.0872	0.6360	0.8557	0.037*
C6	0.3529 (3)	0.59492 (7)	0.76456 (14)	0.0251 (4)
H6A	0.3789	0.5524	0.7970	0.030*
C7	0.4690 (3)	0.62255 (7)	0.67623 (14)	0.0214 (3)
C8	0.9055 (3)	0.61459 (8)	0.45521 (14)	0.0230 (3)
H8A	1.0242	0.5863	0.5079	0.028*
H8B	0.9989	0.6512	0.4282	0.028*
C9	0.7814 (3)	0.57612 (7)	0.34506 (14)	0.0240 (3)
H9A	0.7018	0.5370	0.3721	0.029*
H9B	0.6515	0.6029	0.2962	0.029*
C10	0.7647 (3)	0.56615 (9)	0.03536 (15)	0.0304 (4)
H10A	0.7739	0.5893	−0.0401	0.046*
H10B	0.6024	0.5735	0.0580	0.046*
H10C	0.7883	0.5196	0.0237	0.046*
C11	0.7287 (3)	0.74663 (8)	0.41881 (14)	0.0267 (4)
H11A	0.6390	0.7879	0.4110	0.040*
H11B	0.7081	0.7252	0.3397	0.040*
H11C	0.9047	0.7547	0.4481	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0228 (2)	0.0234 (2)	0.0228 (2)	−0.00198 (15)	0.00438 (15)	0.00159 (14)
O1	0.0331 (7)	0.0212 (6)	0.0301 (6)	0.0054 (5)	0.0009 (5)	0.0038 (4)
O2	0.0215 (6)	0.0569 (8)	0.0305 (7)	−0.0040 (6)	0.0083 (5)	−0.0009 (6)
O3	0.0553 (9)	0.0209 (6)	0.0401 (7)	−0.0029 (6)	0.0049 (6)	0.0035 (5)
N1	0.0229 (7)	0.0194 (6)	0.0188 (6)	0.0010 (5)	0.0036 (5)	0.0001 (5)
N2	0.0229 (7)	0.0194 (6)	0.0202 (6)	−0.0007 (5)	0.0024 (5)	−0.0013 (5)
N3	0.0360 (9)	0.0285 (7)	0.0253 (7)	0.0150 (7)	0.0128 (6)	0.0074 (6)
C1	0.0220 (8)	0.0197 (7)	0.0196 (7)	−0.0011 (6)	−0.0030 (6)	0.0012 (5)
C2	0.0240 (8)	0.0184 (7)	0.0194 (7)	−0.0029 (6)	−0.0004 (6)	0.0007 (5)
C3	0.0266 (8)	0.0167 (7)	0.0226 (7)	0.0002 (6)	0.0024 (6)	0.0014 (6)
C4	0.0254 (9)	0.0306 (8)	0.0272 (8)	−0.0007 (7)	0.0081 (7)	−0.0049 (7)
C5	0.0311 (10)	0.0349 (9)	0.0265 (9)	−0.0065 (7)	0.0074 (7)	−0.0029 (7)
C6	0.0301 (9)	0.0248 (8)	0.0196 (8)	−0.0065 (7)	0.0022 (6)	0.0007 (6)
C7	0.0237 (8)	0.0197 (7)	0.0192 (7)	−0.0016 (6)	−0.0009 (6)	0.0001 (6)
C8	0.0204 (8)	0.0245 (7)	0.0242 (8)	0.0014 (6)	0.0043 (6)	0.0004 (6)
C9	0.0253 (9)	0.0249 (8)	0.0232 (8)	0.0021 (6)	0.0080 (6)	−0.0010 (6)
C10	0.0217 (9)	0.0424 (10)	0.0272 (9)	−0.0040 (7)	0.0046 (7)	−0.0043 (7)
C11	0.0316 (9)	0.0227 (8)	0.0259 (8)	−0.0020 (7)	0.0053 (7)	0.0033 (6)

Geometric parameters (Å, º) top

S1—O2	1.4371 (12)	C4—C5	1.380 (2)
S1—O3	1.4405 (12)	C4—H4A	0.9500
S1—N3	1.5952 (14)	C5—C6	1.399 (2)
S1—C10	1.7563 (17)	C5—H5A	0.9500
O1—C1	1.2378 (17)	C6—C7	1.389 (2)
N1—C1	1.3890 (19)	C6—H6A	0.9500
N1—C2	1.4179 (19)	C8—C9	1.526 (2)
N1—C8	1.4731 (19)	C8—H8A	0.9900
N2—C4	1.3687 (19)	C8—H8B	0.9900
N2—C7	1.3907 (19)	C9—H9A	0.9900
N2—C3	1.3973 (19)	C9—H9B	0.9900
N3—C9	1.4616 (19)	C10—H10A	0.9800
N3—H1N3	0.82 (2)	C10—H10B	0.9800
C1—C7	1.438 (2)	C10—H10C	0.9800
C2—C3	1.338 (2)	C11—H11A	0.9800
C2—C11	1.506 (2)	C11—H11B	0.9800
C3—H3A	0.9500	C11—H11C	0.9800

O2—S1—O3	118.97 (8)	C7—C6—C5	107.08 (14)
O2—S1—N3	107.32 (8)	C7—C6—H6A	126.5
O3—S1—N3	108.98 (8)	C5—C6—H6A	126.5
O2—S1—C10	107.98 (8)	C6—C7—N2	107.42 (13)
O3—S1—C10	106.48 (8)	C6—C7—C1	132.03 (14)
N3—S1—C10	106.47 (8)	N2—C7—C1	120.49 (13)
C1—N1—C2	122.30 (13)	N1—C8—C9	111.09 (13)
C1—N1—C8	116.35 (12)	N1—C8—H8A	109.4
C2—N1—C8	121.35 (12)	C9—C8—H8A	109.4
C4—N2—C7	109.25 (13)	N1—C8—H8B	109.4
C4—N2—C3	129.93 (13)	C9—C8—H8B	109.4
C7—N2—C3	120.82 (13)	H8A—C8—H8B	108.0
C9—N3—S1	122.41 (12)	N3—C9—C8	110.19 (13)
C9—N3—H1N3	120.1 (14)	N3—C9—H9A	109.6
S1—N3—H1N3	117.2 (14)	C8—C9—H9A	109.6
O1—C1—N1	120.88 (14)	N3—C9—H9B	109.6
O1—C1—C7	123.13 (14)	C8—C9—H9B	109.6
N1—C1—C7	115.99 (13)	H9A—C9—H9B	108.1
C3—C2—N1	120.38 (13)	S1—C10—H10A	109.5
C3—C2—C11	121.40 (14)	S1—C10—H10B	109.5
N1—C2—C11	118.19 (13)	H10A—C10—H10B	109.5
C2—C3—N2	119.95 (14)	S1—C10—H10C	109.5
C2—C3—H3A	120.0	H10A—C10—H10C	109.5
N2—C3—H3A	120.0	H10B—C10—H10C	109.5
N2—C4—C5	107.54 (14)	C2—C11—H11A	109.5
N2—C4—H4A	126.2	C2—C11—H11B	109.5
C5—C4—H4A	126.2	H11A—C11—H11B	109.5
C4—C5—C6	108.71 (15)	C2—C11—H11C	109.5
C4—C5—H5A	125.6	H11A—C11—H11C	109.5
C6—C5—H5A	125.6	H11B—C11—H11C	109.5

O2—S1—N3—C9	163.37 (13)	N2—C4—C5—C6	−0.44 (19)
O3—S1—N3—C9	33.29 (16)	C4—C5—C6—C7	0.49 (19)
C10—S1—N3—C9	−81.20 (15)	C5—C6—C7—N2	−0.36 (17)
C2—N1—C1—O1	178.48 (14)	C5—C6—C7—C1	−177.60 (16)
C8—N1—C1—O1	−1.4 (2)	C4—N2—C7—C6	0.09 (17)
C2—N1—C1—C7	−1.1 (2)	C3—N2—C7—C6	179.43 (13)
C8—N1—C1—C7	179.04 (12)	C4—N2—C7—C1	177.72 (14)
C1—N1—C2—C3	−0.4 (2)	C3—N2—C7—C1	−2.9 (2)
C8—N1—C2—C3	179.51 (14)	O1—C1—C7—C6	0.1 (3)
C1—N1—C2—C11	177.87 (14)	N1—C1—C7—C6	179.63 (15)
C8—N1—C2—C11	−2.2 (2)	O1—C1—C7—N2	−176.85 (14)
N1—C2—C3—N2	0.2 (2)	N1—C1—C7—N2	2.7 (2)
C11—C2—C3—N2	−177.95 (14)	C1—N1—C8—C9	83.75 (16)
C4—N2—C3—C2	−179.39 (16)	C2—N1—C8—C9	−96.15 (16)
C7—N2—C3—C2	1.4 (2)	S1—N3—C9—C8	−100.44 (15)
C7—N2—C4—C5	0.21 (18)	N1—C8—C9—N3	174.55 (12)
C3—N2—C4—C5	−179.05 (15)

Hydrogen-bond geometry (Å, º) top

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

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···O1ⁱ	0.82 (2)	1.99 (2)	2.7923 (18)	168 (2)
C4—H4A···O3ⁱⁱ	0.95	2.36	3.258 (2)	157
C8—H8A···Cg1ⁱⁱⁱ	0.99	2.96	3.5153 (19)	116

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x−1, −y+3/2, z+1/2; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₅N₃O₃S
M_r	269.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	5.492 (1), 20.631 (4), 11.212 (2)
β (°)	99.953 (6)
V (Å³)	1251.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.18 × 0.12 × 0.10

Data collection
Diffractometer	Rigaku Saturn CCD area-detector
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.954, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	9267, 2969, 2499
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.105, 1.05
No. of reflections	2969
No. of parameters	169
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.46

Computer programs: CrystalClear (Rigaku, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···O1ⁱ	0.82 (2)	1.99 (2)	2.7923 (18)	168 (2)
C4—H4A···O3ⁱⁱ	0.95	2.36	3.258 (2)	157
C8—H8A···Cg1ⁱⁱⁱ	0.99	2.96	3.5153 (19)	116

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x−1, −y+3/2, z+1/2; (iii) x+1, y, z.

Footnotes

‡Additional correspondence author, e-mail: suchada.c@psu.ac.th. Thomson Reuters ResearcherID: A-5085-2009.

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

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

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References

organic compounds

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