1,3,6-Trimethyl-pyrano[4,3-b]pyrrol-4(1H)-one.

All the non-H atoms of the title compound, C(10)H(11)NO(2), are almost coplanar [maximum deviation = 0.040 (3) Å]. The crystal structure is stabilized by C-H⋯O hydrogen bonds.

Related literature

For general background to isocoumarins, see: Barry (1964 ▶). For related structures, see: Abid et al. (2006 ▶, 2008 ▶); Hathwar et al. (2007 ▶).

Experimental

Crystal data

C10H11NO2

M = 177.20

Monoclinic,

a = 7.5556 (7) Å

b = 8.4819 (8) Å

c = 14.3081 (14) Å

β = 93.870 (6)°

V = 914.86 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.33 × 0.28 × 0.15 mm

Data collection

Oxford Xcalibur Eos (Nova) CCD detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 ▶) T min = 0.916, T max = 0.987

7291 measured reflections

1692 independent reflections

1176 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.179

S = 1.18

1692 reflections

122 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: WinGX (Farrugia, 1997 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809055627/bt5154sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055627/bt5154Isup2.hkl

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

C10H11NO2	F(000) = 376
Mr = 177.20	Dx = 1.287 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1235 reflections
a = 7.5556 (7) Å	θ = 2.9–20.4°
b = 8.4819 (8) Å	µ = 0.09 mm−1
c = 14.3081 (14) Å	T = 295 K
β = 93.870 (6)°	Block, colorless
V = 914.86 (15) Å3	0.33 × 0.28 × 0.15 mm
Z = 4

Oxford Xcalibur Eos (Nova) CCD detector diffractometer	1692 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1176 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω scans	θmax = 25.5°, θmin = 2.8°
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	h = −9→9
Tmin = 0.916, Tmax = 0.987	k = −9→10
7291 measured reflections	l = −17→17

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)] = 0.051	H-atom parameters constrained
wR(F2) = 0.179	w = 1/[σ2(Fo2) + (0.0888P)2 + 0.144P] where P = (Fo2 + 2Fc2)/3
S = 1.18	(Δ/σ)max < 0.001
1692 reflections	Δρmax = 0.27 e Å−3
122 parameters	Δρmin = −0.18 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: 0.004 (1)

	x	y	z	Uiso*/Ueq
N1	0.1293 (2)	0.4172 (2)	0.87406 (12)	0.0412 (5)
O1	0.3720 (3)	0.1280 (3)	1.12304 (13)	0.0818 (7)
O2	0.3792 (2)	0.3881 (2)	1.13262 (10)	0.0586 (6)
C1	0.1778 (3)	0.1674 (3)	0.92158 (16)	0.0466 (6)
C2	0.1079 (3)	0.2591 (3)	0.85100 (16)	0.0466 (6)
H2	0.0534	0.2216	0.7951	0.056*
C3	0.2612 (3)	0.5620 (3)	1.01528 (16)	0.0460 (6)
H3	0.2372	0.6633	0.9929	0.055*
C4	0.3421 (3)	0.5382 (3)	1.09968 (17)	0.0507 (7)
C5	0.3331 (3)	0.2497 (3)	1.08310 (16)	0.0526 (7)
C6	0.2454 (3)	0.2744 (3)	0.99253 (14)	0.0420 (6)
C7	0.2128 (3)	0.4269 (2)	0.96087 (14)	0.0389 (6)
C8	0.4000 (4)	0.6605 (4)	1.1693 (2)	0.0749 (9)
H8A	0.3742	0.7631	1.1435	0.112*
H8B	0.5253	0.6511	1.1842	0.112*
H8C	0.3380	0.6465	1.2251	0.112*
C9	0.1882 (4)	−0.0092 (3)	0.9237 (2)	0.0702 (9)
H9A	0.1145	−0.0518	0.8725	0.105*
H9B	0.1480	−0.0472	0.9818	0.105*
H9C	0.3087	−0.0416	0.9181	0.105*
C10	0.0743 (4)	0.5500 (3)	0.81496 (17)	0.0551 (7)
H10A	0.0008	0.6192	0.8487	0.083*
H10B	0.0085	0.5123	0.7597	0.083*
H10C	0.1771	0.6063	0.7974	0.083*

	U11	U22	U33	U12	U13	U23
N1	0.0466 (11)	0.0379 (11)	0.0382 (10)	0.0025 (8)	−0.0049 (8)	0.0018 (8)
O1	0.1038 (17)	0.0781 (16)	0.0623 (12)	0.0317 (12)	−0.0034 (11)	0.0266 (11)
O2	0.0562 (11)	0.0777 (14)	0.0403 (9)	0.0065 (9)	−0.0082 (7)	−0.0015 (9)
C1	0.0506 (13)	0.0375 (13)	0.0521 (14)	−0.0005 (11)	0.0074 (11)	−0.0007 (11)
C2	0.0488 (13)	0.0463 (14)	0.0442 (12)	−0.0021 (11)	−0.0008 (10)	−0.0089 (12)
C3	0.0474 (13)	0.0415 (14)	0.0489 (13)	−0.0035 (10)	0.0016 (10)	−0.0050 (10)
C4	0.0443 (13)	0.0604 (17)	0.0471 (13)	−0.0021 (12)	0.0015 (10)	−0.0097 (11)
C5	0.0541 (15)	0.0589 (17)	0.0448 (13)	0.0102 (13)	0.0022 (11)	0.0066 (13)
C6	0.0432 (12)	0.0416 (13)	0.0409 (12)	0.0030 (10)	0.0017 (9)	0.0050 (10)
C7	0.0392 (12)	0.0400 (13)	0.0372 (11)	0.0023 (10)	0.0005 (9)	0.0033 (9)
C8	0.0654 (18)	0.096 (2)	0.0630 (17)	−0.0162 (17)	−0.0004 (13)	−0.0329 (16)
C9	0.085 (2)	0.0395 (16)	0.087 (2)	0.0000 (15)	0.0159 (16)	−0.0025 (15)
C10	0.0634 (16)	0.0556 (17)	0.0450 (13)	0.0061 (13)	−0.0055 (11)	0.0116 (11)

N1—C7	1.357 (3)	C4—C8	1.483 (4)
N1—C2	1.388 (3)	C5—C6	1.431 (3)
N1—C10	1.452 (3)	C6—C7	1.387 (3)
O1—C5	1.206 (3)	C8—H8A	0.9600
O2—C4	1.380 (3)	C8—H8B	0.9600
O2—C5	1.403 (3)	C8—H8C	0.9600
C1—C2	1.353 (3)	C9—H9A	0.9600
C1—C6	1.430 (3)	C9—H9B	0.9600
C1—C9	1.500 (4)	C9—H9C	0.9600
C2—H2	0.9300	C10—H10A	0.9600
C3—C4	1.332 (3)	C10—H10B	0.9600
C3—C7	1.419 (3)	C10—H10C	0.9600
C3—H3	0.9300
C7—N1—C2	108.41 (19)	N1—C7—C6	107.66 (19)
C7—N1—C10	125.64 (19)	N1—C7—C3	129.6 (2)
C2—N1—C10	125.94 (19)	C6—C7—C3	122.7 (2)
C4—O2—C5	124.21 (19)	C4—C8—H8A	109.5
C2—C1—C6	105.5 (2)	C4—C8—H8B	109.5
C2—C1—C9	127.3 (2)	H8A—C8—H8B	109.5
C6—C1—C9	127.2 (2)	C4—C8—H8C	109.5
C1—C2—N1	110.2 (2)	H8A—C8—H8C	109.5
C1—C2—H2	124.9	H8B—C8—H8C	109.5
N1—C2—H2	124.9	C1—C9—H9A	109.5
C4—C3—C7	117.4 (2)	C1—C9—H9B	109.5
C4—C3—H3	121.3	H9A—C9—H9B	109.5
C7—C3—H3	121.3	C1—C9—H9C	109.5
C3—C4—O2	121.3 (2)	H9A—C9—H9C	109.5
C3—C4—C8	126.8 (3)	H9B—C9—H9C	109.5
O2—C4—C8	111.9 (2)	N1—C10—H10A	109.5
O1—C5—O2	115.6 (2)	N1—C10—H10B	109.5
O1—C5—C6	129.6 (3)	H10A—C10—H10B	109.5
O2—C5—C6	114.8 (2)	N1—C10—H10C	109.5
C7—C6—C1	108.3 (2)	H10A—C10—H10C	109.5
C7—C6—C5	119.6 (2)	H10B—C10—H10C	109.5
C1—C6—C5	132.2 (2)
C6—C1—C2—N1	0.3 (2)	O1—C5—C6—C7	179.4 (2)
C9—C1—C2—N1	−177.7 (2)	O2—C5—C6—C7	0.0 (3)
C7—N1—C2—C1	−0.5 (2)	O1—C5—C6—C1	−0.4 (4)
C10—N1—C2—C1	178.7 (2)	O2—C5—C6—C1	−179.8 (2)
C7—C3—C4—O2	0.6 (3)	C2—N1—C7—C6	0.4 (2)
C7—C3—C4—C8	−178.2 (2)	C10—N1—C7—C6	−178.74 (19)
C5—O2—C4—C3	−1.5 (3)	C2—N1—C7—C3	−178.8 (2)
C5—O2—C4—C8	177.5 (2)	C10—N1—C7—C3	2.1 (4)
C4—O2—C5—O1	−178.4 (2)	C1—C6—C7—N1	−0.2 (2)
C4—O2—C5—C6	1.1 (3)	C5—C6—C7—N1	179.96 (18)
C2—C1—C6—C7	−0.1 (2)	C1—C6—C7—C3	179.06 (19)
C9—C1—C6—C7	177.9 (2)	C5—C6—C7—C3	−0.8 (3)
C2—C1—C6—C5	179.7 (2)	C4—C3—C7—N1	179.6 (2)
C9—C1—C6—C5	−2.2 (4)	C4—C3—C7—C6	0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O1i	0.96	2.46	3.404 (3)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O1i	0.96	2.46	3.404 (3)	170

Symmetry code: (i) .