N-[2-(3-Methyl-1-oxo-1,2-dihydro-pyrrolo-[1,2-a]pyrazin-2-yl)eth-yl]methane-sulfonamide.

In the title compound, C(11)H(15)N(3)O(3)S, the dihedral angle between the five- and six-membered rings is 1.13 (18)°. The ethyl-methane-sulfonamide group is in a (+)synclinal conformation. In the crystal, inter-molecular N-H⋯O and C-H⋯O hydrogen-bond inter-actions link mol-ecules into zigzag ribbons parallel to the b axis. The ribbons are further connected by C-H⋯π inter-actions.

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 = 269.33

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.105

S = 1.05

2969 reflections

169 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.46 e Å−3

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 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026115/rz2471Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H15N3O3S	F(000) = 568
Mr = 269.33	Dx = 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

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

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(Fo2) + (0.058P)2 + 0.0584P] where P = (Fo2 + 2Fc2)/3
2969 reflections	(Δ/σ)max = 0.001
169 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .