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

The mol-ecule of the title compound, C(13)H(9)NO(2), is slightly twisted with a dihedral angle of 4.85 (9)° between the nine-membered ring system and the phenyl ring. The nine non-H atoms of the 1H-pyrrolo[2,1-c][1,4]oxazin-1-one system are coplanar [r.m.s. deviation = 0.0122 (2) Å]. In the crystal, weak inter-molecular C-H⋯O inter-actions link mol-ecules into chains along [10]. The crystal studied was an inversion twin with a 0.48624 (9):0.51376 (9) domain ratio.

Related literature

For the biological activity and applications of pyrrolo[1,2-a]pyrazine derivatives, see: Bélanger et al. (1983 ▶); Fu et al. (2002 ▶); Micheli et al. (2008 ▶). For a related structure, see: Khan et al. (2010 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H9NO2

M = 211.21

Monoclinic,

a = 5.870 (1) Å

b = 3.8345 (7) Å

c = 21.733 (4) Å

β = 91.059 (7)°

V = 489.09 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 113 K

0.22 × 0.18 × 0.08 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.979, T max = 0.992

4358 measured reflections

1222 independent reflections

1092 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.085

S = 1.10

1222 reflections

147 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.20 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: 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/S1600536810017940/rz2449sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017940/rz2449Isup2.hkl

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

C13H9NO2	F(000) = 220
Mr = 211.21	Dx = 1.434 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1222 reflections
a = 5.870 (1) Å	θ = 2.8–27.0°
b = 3.8345 (7) Å	µ = 0.10 mm−1
c = 21.733 (4) Å	T = 113 K
β = 91.059 (7)°	Needle, colourless
V = 489.09 (15) Å3	0.22 × 0.18 × 0.08 mm
Z = 2

Rigaku Saturn CCD area-detector diffractometer	1222 independent reflections
Radiation source: rotating anode	1092 reflections with I > 2σ(I)
multilayer	Rint = 0.032
Detector resolution: 14.63 pixels mm-1	θmax = 27.0°, θmin = 2.8°
ω and φ scans	h = −7→7
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −4→4
Tmin = 0.979, Tmax = 0.992	l = −26→27
4358 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)] = 0.031	H-atom parameters constrained
wR(F2) = 0.085	w = 1/[σ2(Fo2) + (0.050P)2] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
1222 reflections	Δρmax = 0.20 e Å−3
147 parameters	Δρmin = −0.19 e Å−3
1 restraint	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.037 (9)

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	0.4797 (2)	0.4846 (4)	0.25405 (5)	0.0201 (4)
O2	0.7147 (2)	0.7726 (4)	0.31664 (6)	0.0273 (4)
N1	0.1877 (2)	0.3508 (4)	0.34783 (7)	0.0181 (4)
C1	0.0686 (3)	0.3143 (6)	0.40070 (8)	0.0219 (5)
H1	−0.0763	0.2067	0.4044	0.026*
C2	0.1959 (3)	0.4614 (6)	0.44782 (8)	0.0232 (5)
H2	0.1546	0.4700	0.4899	0.028*
C3	0.3965 (3)	0.5960 (6)	0.42329 (9)	0.0230 (5)
H3	0.5148	0.7140	0.4453	0.028*
C4	0.3895 (3)	0.5244 (5)	0.36106 (8)	0.0186 (4)
C5	0.5406 (3)	0.6064 (6)	0.31182 (8)	0.0198 (4)
C6	0.2775 (3)	0.3039 (6)	0.24323 (8)	0.0177 (4)
C7	0.1330 (3)	0.2396 (6)	0.28844 (8)	0.0189 (4)
H7	−0.0057	0.1192	0.2802	0.023*
C8	0.2448 (3)	0.1991 (6)	0.17857 (8)	0.0186 (4)
C9	0.4150 (3)	0.2573 (6)	0.13567 (8)	0.0223 (5)
H9	0.5540	0.3651	0.1483	0.027*
C10	0.3819 (4)	0.1584 (6)	0.07468 (9)	0.0258 (5)
H10	0.4987	0.1992	0.0459	0.031*
C11	0.1813 (4)	0.0015 (6)	0.05544 (8)	0.0242 (5)
H11	0.1596	−0.0651	0.0136	0.029*
C12	0.0115 (3)	−0.0580 (6)	0.09787 (8)	0.0248 (5)
H12	−0.1273	−0.1651	0.0849	0.030*
C13	0.0429 (3)	0.0377 (6)	0.15879 (8)	0.0220 (5)
H13	−0.0738	−0.0068	0.1875	0.026*

	U11	U22	U33	U12	U13	U23
O1	0.0165 (7)	0.0229 (8)	0.0210 (6)	−0.0045 (6)	0.0017 (5)	0.0005 (7)
O2	0.0190 (7)	0.0308 (9)	0.0321 (8)	−0.0093 (7)	−0.0014 (5)	0.0000 (7)
N1	0.0163 (8)	0.0198 (10)	0.0183 (8)	−0.0017 (7)	0.0007 (6)	0.0014 (7)
C1	0.0206 (10)	0.0251 (12)	0.0202 (9)	0.0008 (9)	0.0047 (7)	0.0043 (9)
C2	0.0263 (10)	0.0249 (12)	0.0185 (9)	0.0048 (10)	0.0025 (7)	0.0021 (9)
C3	0.0233 (10)	0.0222 (12)	0.0234 (9)	0.0015 (9)	−0.0033 (7)	−0.0017 (9)
C4	0.0161 (9)	0.0173 (12)	0.0224 (9)	0.0000 (8)	−0.0019 (7)	0.0001 (9)
C5	0.0183 (10)	0.0170 (11)	0.0240 (9)	0.0002 (9)	−0.0017 (7)	0.0007 (9)
C6	0.0146 (9)	0.0166 (11)	0.0220 (9)	−0.0019 (8)	−0.0010 (7)	0.0017 (8)
C7	0.0172 (9)	0.0207 (11)	0.0187 (8)	−0.0025 (8)	−0.0012 (7)	0.0002 (9)
C8	0.0193 (9)	0.0168 (11)	0.0197 (9)	0.0027 (8)	0.0009 (7)	0.0020 (8)
C9	0.0202 (10)	0.0237 (12)	0.0229 (9)	0.0017 (9)	0.0011 (7)	0.0015 (10)
C10	0.0289 (11)	0.0275 (13)	0.0211 (9)	0.0049 (10)	0.0064 (8)	0.0034 (9)
C11	0.0310 (11)	0.0237 (12)	0.0178 (9)	0.0066 (9)	−0.0020 (7)	−0.0001 (9)
C12	0.0239 (10)	0.0248 (12)	0.0255 (10)	0.0016 (10)	−0.0042 (7)	−0.0020 (10)
C13	0.0199 (10)	0.0243 (13)	0.0219 (9)	0.0000 (9)	0.0030 (7)	0.0003 (10)

O1—C5	1.380 (2)	C6—C8	1.471 (2)
O1—C6	1.391 (2)	C7—H7	0.9500
O2—C5	1.207 (2)	C8—C9	1.397 (2)
N1—C1	1.363 (2)	C8—C13	1.397 (3)
N1—C4	1.384 (2)	C9—C10	1.389 (3)
N1—C7	1.391 (2)	C9—H9	0.9500
C1—C2	1.377 (3)	C10—C11	1.380 (3)
C1—H1	0.9500	C10—H10	0.9500
C2—C3	1.400 (3)	C11—C12	1.389 (3)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.380 (3)	C12—C13	1.383 (3)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.438 (2)	C13—H13	0.9500
C6—C7	1.333 (2)
C5—O1—C6	121.88 (14)	C6—C7—N1	119.21 (18)
C1—N1—C4	108.95 (15)	C6—C7—H7	120.4
C1—N1—C7	129.57 (17)	N1—C7—H7	120.4
C4—N1—C7	121.48 (15)	C9—C8—C13	118.58 (17)
N1—C1—C2	107.74 (17)	C9—C8—C6	120.77 (17)
N1—C1—H1	126.1	C13—C8—C6	120.65 (16)
C2—C1—H1	126.1	C10—C9—C8	120.26 (19)
C1—C2—C3	108.45 (17)	C10—C9—H9	119.9
C1—C2—H2	125.8	C8—C9—H9	119.9
C3—C2—H2	125.8	C11—C10—C9	120.78 (17)
C4—C3—C2	106.83 (18)	C11—C10—H10	119.6
C4—C3—H3	126.6	C9—C10—H10	119.6
C2—C3—H3	126.6	C10—C11—C12	119.29 (18)
C3—C4—N1	108.03 (16)	C10—C11—H11	120.4
C3—C4—C5	132.71 (19)	C12—C11—H11	120.4
N1—C4—C5	119.21 (16)	C13—C12—C11	120.47 (19)
O2—C5—O1	117.52 (16)	C13—C12—H12	119.8
O2—C5—C4	125.73 (18)	C11—C12—H12	119.8
O1—C5—C4	116.75 (16)	C12—C13—C8	120.62 (17)
C7—C6—O1	121.35 (17)	C12—C13—H13	119.7
C7—C6—C8	125.48 (18)	C8—C13—H13	119.7
O1—C6—C8	113.17 (15)
C4—N1—C1—C2	−0.7 (2)	C5—O1—C6—C8	179.70 (17)
C7—N1—C1—C2	178.7 (2)	O1—C6—C7—N1	−1.1 (3)
N1—C1—C2—C3	0.9 (2)	C8—C6—C7—N1	179.16 (18)
C1—C2—C3—C4	−0.7 (2)	C1—N1—C7—C6	−179.8 (2)
C2—C3—C4—N1	0.3 (2)	C4—N1—C7—C6	−0.5 (3)
C2—C3—C4—C5	177.6 (2)	C7—C6—C8—C9	−175.2 (2)
C1—N1—C4—C3	0.2 (2)	O1—C6—C8—C9	5.0 (3)
C7—N1—C4—C3	−179.20 (19)	C7—C6—C8—C13	4.5 (3)
C1—N1—C4—C5	−177.49 (18)	O1—C6—C8—C13	−175.29 (19)
C7—N1—C4—C5	3.1 (3)	C13—C8—C9—C10	0.5 (3)
C6—O1—C5—O2	−177.16 (18)	C6—C8—C9—C10	−179.8 (2)
C6—O1—C5—C4	2.6 (3)	C8—C9—C10—C11	0.0 (3)
C3—C4—C5—O2	−1.3 (4)	C9—C10—C11—C12	−0.1 (4)
N1—C4—C5—O2	175.7 (2)	C10—C11—C12—C13	−0.2 (4)
C3—C4—C5—O1	178.9 (2)	C11—C12—C13—C8	0.7 (4)
N1—C4—C5—O1	−4.0 (3)	C9—C8—C13—C12	−0.8 (3)
C5—O1—C6—C7	−0.1 (3)	C6—C8—C13—C12	179.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2i	0.95	2.27	3.109 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O2i	0.95	2.27	3.109 (2)	147

Symmetry code: (i) .