3-Methyl-1H-pyrrolo[2,1-c][1,4]oxazin-1-one.

In the title mol-ecule, C(8)H(7)NO(2), all the non-H atoms lie essentially in the same plane (r.m.s. deviation = 0.019 Å) In the crystal structure, weak inter-molecular C-H⋯O inter-actions link mol-ecules into chains along [100]. In addition, there are π-π stacking inter-actions between mol-ecules related by the c-glide plane, with alternating centroid-centroid distances of 3.434 (2) and 3.639 (2) Å.

Related literature

For the synthesis and applications of the title compound, see: Dumas et al. (1988 ▶); Micheli et al. (2008 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H7NO2

M = 149.15

Monoclinic,

a = 6.915 (4) Å

b = 15.502 (8) Å

c = 7.024 (4) Å

β = 112.866 (8)°

V = 693.8 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 113 K

0.32 × 0.28 × 0.08 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.967, T max = 0.992

4630 measured reflections

1223 independent reflections

957 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.091

S = 1.01

1223 reflections

102 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: CrystalClear.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810006951/pv2260sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006951/pv2260Isup2.hkl

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

C8H7NO2	F(000) = 312
Mr = 149.15	Dx = 1.428 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2364 reflections
a = 6.915 (4) Å	θ = 3.1–27.9°
b = 15.502 (8) Å	µ = 0.10 mm−1
c = 7.024 (4) Å	T = 113 K
β = 112.866 (8)°	Prism, colorless
V = 693.8 (6) Å3	0.32 × 0.28 × 0.08 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	1223 independent reflections
Radiation source: rotating anode	957 reflections with I > 2σ(I)
multilayer	Rint = 0.044
Detector resolution: 14.63 pixels mm-1	θmax = 25.0°, θmin = 3.4°
ω and φ scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −12→18
Tmin = 0.967, Tmax = 0.992	l = −8→8
4630 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035	H-atom parameters constrained
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0505P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.002
1223 reflections	Δρmax = 0.23 e Å−3
102 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.025 (6)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O1	0.45807 (13)	0.61029 (5)	0.34499 (13)	0.0259 (3)
O2	0.78058 (13)	0.65952 (7)	0.42312 (15)	0.0384 (3)
N1	0.29846 (17)	0.77385 (7)	0.30630 (16)	0.0221 (3)
C1	0.2544 (2)	0.85965 (8)	0.2913 (2)	0.0287 (4)
H1	0.1204	0.8847	0.2615	0.034*
C2	0.4378 (2)	0.90383 (9)	0.32687 (19)	0.0323 (4)
H2	0.4525	0.9647	0.3252	0.039*
C3	0.5987 (2)	0.84336 (9)	0.3659 (2)	0.0304 (4)
H3	0.7423	0.8555	0.3960	0.037*
C4	0.5104 (2)	0.76289 (8)	0.35257 (18)	0.0237 (4)
C5	0.5972 (2)	0.67754 (8)	0.3770 (2)	0.0250 (4)
C6	0.24605 (19)	0.62433 (8)	0.30253 (19)	0.0228 (3)
C7	0.1665 (2)	0.70294 (8)	0.28336 (19)	0.0235 (3)
H7	0.0216	0.7111	0.2544	0.028*
C8	0.1316 (2)	0.54197 (8)	0.2877 (2)	0.0316 (4)
H8A	−0.0147	0.5542	0.2654	0.047*
H8B	0.1981	0.5093	0.4162	0.047*
H8C	0.1357	0.5080	0.1716	0.047*

	U11	U22	U33	U12	U13	U23
O1	0.0236 (5)	0.0252 (5)	0.0306 (5)	0.0023 (4)	0.0125 (4)	0.0013 (4)
O2	0.0227 (6)	0.0449 (7)	0.0502 (7)	0.0045 (4)	0.0170 (5)	0.0071 (5)
N1	0.0238 (6)	0.0216 (6)	0.0213 (6)	0.0004 (4)	0.0093 (4)	0.0011 (4)
C1	0.0359 (8)	0.0227 (7)	0.0276 (7)	0.0059 (6)	0.0123 (6)	0.0015 (6)
C2	0.0449 (10)	0.0223 (7)	0.0268 (8)	−0.0076 (7)	0.0110 (7)	−0.0004 (6)
C3	0.0296 (8)	0.0338 (8)	0.0265 (7)	−0.0083 (6)	0.0093 (6)	0.0009 (6)
C4	0.0212 (7)	0.0299 (8)	0.0197 (7)	−0.0018 (6)	0.0076 (5)	0.0018 (6)
C5	0.0225 (8)	0.0307 (8)	0.0235 (7)	−0.0006 (6)	0.0108 (6)	0.0024 (6)
C6	0.0187 (7)	0.0289 (8)	0.0212 (7)	−0.0003 (6)	0.0081 (5)	−0.0003 (6)
C7	0.0197 (7)	0.0258 (7)	0.0254 (7)	−0.0008 (6)	0.0091 (5)	0.0006 (6)
C8	0.0307 (8)	0.0250 (7)	0.0375 (8)	−0.0026 (6)	0.0114 (7)	−0.0009 (6)

O1—C5	1.3767 (16)	C3—C4	1.3761 (19)
O1—C6	1.3950 (17)	C3—H3	0.9500
O2—C5	1.2128 (16)	C4—C5	1.4356 (19)
N1—C1	1.3596 (18)	C6—C7	1.3223 (19)
N1—C4	1.3826 (19)	C6—C8	1.4844 (18)
N1—C7	1.3976 (18)	C7—H7	0.9500
C1—C2	1.376 (2)	C8—H8A	0.9800
C1—H1	0.9500	C8—H8B	0.9800
C2—C3	1.398 (2)	C8—H8C	0.9800
C2—H2	0.9500
C5—O1—C6	121.78 (10)	O2—C5—O1	117.45 (12)
C1—N1—C4	108.89 (11)	O2—C5—C4	126.13 (12)
C1—N1—C7	130.07 (12)	O1—C5—C4	116.42 (12)
C4—N1—C7	121.03 (11)	C7—C6—O1	121.79 (12)
N1—C1—C2	108.03 (13)	C7—C6—C8	126.58 (13)
N1—C1—H1	126.0	O1—C6—C8	111.61 (11)
C2—C1—H1	126.0	C6—C7—N1	119.06 (13)
C1—C2—C3	108.01 (13)	C6—C7—H7	120.5
C1—C2—H2	126.0	N1—C7—H7	120.5
C3—C2—H2	126.0	C6—C8—H8A	109.5
C4—C3—C2	107.21 (13)	C6—C8—H8B	109.5
C4—C3—H3	126.4	H8A—C8—H8B	109.5
C2—C3—H3	126.4	C6—C8—H8C	109.5
C3—C4—N1	107.85 (12)	H8A—C8—H8C	109.5
C3—C4—C5	132.32 (14)	H8B—C8—H8C	109.5
N1—C4—C5	119.83 (11)
C4—N1—C1—C2	0.31 (14)	C6—O1—C5—C4	−3.46 (18)
C7—N1—C1—C2	179.99 (12)	C3—C4—C5—O2	2.3 (3)
N1—C1—C2—C3	−0.36 (16)	N1—C4—C5—O2	−177.76 (12)
C1—C2—C3—C4	0.26 (16)	C3—C4—C5—O1	−177.79 (13)
C2—C3—C4—N1	−0.07 (15)	N1—C4—C5—O1	2.12 (18)
C2—C3—C4—C5	179.84 (13)	C5—O1—C6—C7	2.52 (18)
C1—N1—C4—C3	−0.15 (14)	C5—O1—C6—C8	−176.31 (11)
C7—N1—C4—C3	−179.86 (11)	O1—C6—C7—N1	0.00 (19)
C1—N1—C4—C5	179.92 (12)	C8—C6—C7—N1	178.64 (12)
C7—N1—C4—C5	0.22 (18)	C1—N1—C7—C6	179.04 (12)
C6—O1—C5—O2	176.42 (11)	C4—N1—C7—C6	−1.32 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2i	0.95	2.52	3.252 (3)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O2i	0.95	2.52	3.252 (3)	134

Symmetry code: (i) .