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

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1,3,6-Tri­methyl­pyrano[4,3-b]pyrrol-4(1H)-one

aSchool of Advanced Sciences, VIT University, Vellore 632 014, Tamil Nadu, India, bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560012, Karnataka, India, and cDepartment of Chemistry, Aarupadai Veedu Institute of Technology, Vinayaka Missions University, Paiyanoor, Chennai 603 104, Tamil Nadu, India
*Correspondence e-mail: nawaz_f@yahoo.co.in

(Received 18 December 2009; accepted 28 December 2009; online 16 January 2010)

All the non-H atoms of the title compound, C10H11NO2, 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[Barry, R. D. (1964). Chem. Rev. 64, 229-260.]). For related structures, see: Abid et al. (2006[Abid, O., Rama, N. H., Qadeer, G., Khan, G. S. & Lu, X.-M. (2006). Acta Cryst. E62, o2895-o2896.], 2008[Abid, O.-U.-R., Qadeer, G., Rama, N. H., Ruzicka, A. & Padelkova, Z. (2008). Acta Cryst. E64, o2018.]); Hathwar et al. (2007[Hathwar, V. R., Manivel, P., Nawaz Khan, F. & Guru Row, T. N. (2007). Acta Cryst. E63, o3707.]).

[Scheme 1]

Experimental

Crystal data
  • C10H11NO2

  • Mr = 177.20

  • Monoclinic, P 21 /n

  • 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[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.916, Tmax = 0.987

  • 7291 measured reflections

  • 1692 independent reflections

  • 1176 reflections with I > 2σ(I)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C10—H10B⋯O1i 0.96 2.46 3.404 (3) 170
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and CAMERON (Watkin et al., 1993[Watkin, D. J., Pearce, L. & Prout, C. K. (1993). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.]); software used to prepare material for publication: WinGX (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]).

Supporting information


Comment top

Isocoumarins (Barry, 1964) are also useful intermediates in the synthesis of a variety of important compounds including some carbocyclic and heterocyclic compounds. In view of their natural occurrence, biological activities and utility as synthetic intermediates, we have synthesized the title compound, and reported herein its crystal structure.

Related literature top

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

Experimental top

A mixture of 2-(carboxymethyl)-1, 4-dimethyl-1H-pyrrole-3-carboxylic acid (2 mmol) and acetic anhydride (8 mmol) in the presence of pyridine was refluxed for 4 h. Completion of the reaction was monitored by Thin Layer Chromatography. After completing of the reaction, the mixture was poured into crushed ice. The solids were separated and purified by silica gel column chromatography. The product was obtained with 90% yield.

Refinement top

All the H atoms were positioned geometrically and refined using a riding model, fixing the bond lengths at 0.96 and 0.93 Å for CH3 aromatic CH, respectively. The displacement parameters of the H atoms were constrained as Uiso(H) = 1.2Ueq (1.5Ueq for methyl) of the carrier atom.

Computing details top

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO CCD (Oxford Diffraction, 2009); 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).

Figures top
[Figure 1] Fig. 1. A view of the title complex, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. The packing diagram depicting C—H···O intermolecular interactions.
1,3,6-Trimethylpyrano[4,3-b]pyrrol-4(1H)-one top
Crystal data top
C10H11NO2F(000) = 376
Mr = 177.20Dx = 1.287 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1235 reflections
a = 7.5556 (7) Åθ = 2.9–20.4°
b = 8.4819 (8) ŵ = 0.09 mm1
c = 14.3081 (14) ÅT = 295 K
β = 93.870 (6)°Block, colorless
V = 914.86 (15) Å30.33 × 0.28 × 0.15 mm
Z = 4
Data collection top
Oxford Xcalibur Eos (Nova) CCD detector
diffractometer
1692 independent reflections
Radiation source: Enhance (Mo) X-ray Source1176 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω scansθmax = 25.5°, θmin = 2.8°
Absorption correction: multi-scan
(CrysAlis PRO RED; Oxford Diffraction, 2009)
h = 99
Tmin = 0.916, Tmax = 0.987k = 910
7291 measured reflectionsl = 1717
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-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 reflectionsΔρmax = 0.27 e Å3
122 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.004 (1)
Crystal data top
C10H11NO2V = 914.86 (15) Å3
Mr = 177.20Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.5556 (7) ŵ = 0.09 mm1
b = 8.4819 (8) ÅT = 295 K
c = 14.3081 (14) Å0.33 × 0.28 × 0.15 mm
β = 93.870 (6)°
Data collection top
Oxford Xcalibur Eos (Nova) CCD detector
diffractometer
1692 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO RED; Oxford Diffraction, 2009)
1176 reflections with I > 2σ(I)
Tmin = 0.916, Tmax = 0.987Rint = 0.034
7291 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.179H-atom parameters constrained
S = 1.18Δρmax = 0.27 e Å3
1692 reflectionsΔρmin = 0.18 e Å3
122 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.1293 (2)0.4172 (2)0.87406 (12)0.0412 (5)
O10.3720 (3)0.1280 (3)1.12304 (13)0.0818 (7)
O20.3792 (2)0.3881 (2)1.13262 (10)0.0586 (6)
C10.1778 (3)0.1674 (3)0.92158 (16)0.0466 (6)
C20.1079 (3)0.2591 (3)0.85100 (16)0.0466 (6)
H20.05340.22160.79510.056*
C30.2612 (3)0.5620 (3)1.01528 (16)0.0460 (6)
H30.23720.66330.99290.055*
C40.3421 (3)0.5382 (3)1.09968 (17)0.0507 (7)
C50.3331 (3)0.2497 (3)1.08310 (16)0.0526 (7)
C60.2454 (3)0.2744 (3)0.99253 (14)0.0420 (6)
C70.2128 (3)0.4269 (2)0.96087 (14)0.0389 (6)
C80.4000 (4)0.6605 (4)1.1693 (2)0.0749 (9)
H8A0.37420.76311.14350.112*
H8B0.52530.65111.18420.112*
H8C0.33800.64651.22510.112*
C90.1882 (4)0.0092 (3)0.9237 (2)0.0702 (9)
H9A0.11450.05180.87250.105*
H9B0.14800.04720.98180.105*
H9C0.30870.04160.91810.105*
C100.0743 (4)0.5500 (3)0.81496 (17)0.0551 (7)
H10A0.00080.61920.84870.083*
H10B0.00850.51230.75970.083*
H10C0.17710.60630.79740.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0466 (11)0.0379 (11)0.0382 (10)0.0025 (8)0.0049 (8)0.0018 (8)
O10.1038 (17)0.0781 (16)0.0623 (12)0.0317 (12)0.0034 (11)0.0266 (11)
O20.0562 (11)0.0777 (14)0.0403 (9)0.0065 (9)0.0082 (7)0.0015 (9)
C10.0506 (13)0.0375 (13)0.0521 (14)0.0005 (11)0.0074 (11)0.0007 (11)
C20.0488 (13)0.0463 (14)0.0442 (12)0.0021 (11)0.0008 (10)0.0089 (12)
C30.0474 (13)0.0415 (14)0.0489 (13)0.0035 (10)0.0016 (10)0.0050 (10)
C40.0443 (13)0.0604 (17)0.0471 (13)0.0021 (12)0.0015 (10)0.0097 (11)
C50.0541 (15)0.0589 (17)0.0448 (13)0.0102 (13)0.0022 (11)0.0066 (13)
C60.0432 (12)0.0416 (13)0.0409 (12)0.0030 (10)0.0017 (9)0.0050 (10)
C70.0392 (12)0.0400 (13)0.0372 (11)0.0023 (10)0.0005 (9)0.0033 (9)
C80.0654 (18)0.096 (2)0.0630 (17)0.0162 (17)0.0004 (13)0.0329 (16)
C90.085 (2)0.0395 (16)0.087 (2)0.0000 (15)0.0159 (16)0.0025 (15)
C100.0634 (16)0.0556 (17)0.0450 (13)0.0061 (13)0.0055 (11)0.0116 (11)
Geometric parameters (Å, º) top
N1—C71.357 (3)C4—C81.483 (4)
N1—C21.388 (3)C5—C61.431 (3)
N1—C101.452 (3)C6—C71.387 (3)
O1—C51.206 (3)C8—H8A0.9600
O2—C41.380 (3)C8—H8B0.9600
O2—C51.403 (3)C8—H8C0.9600
C1—C21.353 (3)C9—H9A0.9600
C1—C61.430 (3)C9—H9B0.9600
C1—C91.500 (4)C9—H9C0.9600
C2—H20.9300C10—H10A0.9600
C3—C41.332 (3)C10—H10B0.9600
C3—C71.419 (3)C10—H10C0.9600
C3—H30.9300
C7—N1—C2108.41 (19)N1—C7—C6107.66 (19)
C7—N1—C10125.64 (19)N1—C7—C3129.6 (2)
C2—N1—C10125.94 (19)C6—C7—C3122.7 (2)
C4—O2—C5124.21 (19)C4—C8—H8A109.5
C2—C1—C6105.5 (2)C4—C8—H8B109.5
C2—C1—C9127.3 (2)H8A—C8—H8B109.5
C6—C1—C9127.2 (2)C4—C8—H8C109.5
C1—C2—N1110.2 (2)H8A—C8—H8C109.5
C1—C2—H2124.9H8B—C8—H8C109.5
N1—C2—H2124.9C1—C9—H9A109.5
C4—C3—C7117.4 (2)C1—C9—H9B109.5
C4—C3—H3121.3H9A—C9—H9B109.5
C7—C3—H3121.3C1—C9—H9C109.5
C3—C4—O2121.3 (2)H9A—C9—H9C109.5
C3—C4—C8126.8 (3)H9B—C9—H9C109.5
O2—C4—C8111.9 (2)N1—C10—H10A109.5
O1—C5—O2115.6 (2)N1—C10—H10B109.5
O1—C5—C6129.6 (3)H10A—C10—H10B109.5
O2—C5—C6114.8 (2)N1—C10—H10C109.5
C7—C6—C1108.3 (2)H10A—C10—H10C109.5
C7—C6—C5119.6 (2)H10B—C10—H10C109.5
C1—C6—C5132.2 (2)
C6—C1—C2—N10.3 (2)O1—C5—C6—C7179.4 (2)
C9—C1—C2—N1177.7 (2)O2—C5—C6—C70.0 (3)
C7—N1—C2—C10.5 (2)O1—C5—C6—C10.4 (4)
C10—N1—C2—C1178.7 (2)O2—C5—C6—C1179.8 (2)
C7—C3—C4—O20.6 (3)C2—N1—C7—C60.4 (2)
C7—C3—C4—C8178.2 (2)C10—N1—C7—C6178.74 (19)
C5—O2—C4—C31.5 (3)C2—N1—C7—C3178.8 (2)
C5—O2—C4—C8177.5 (2)C10—N1—C7—C32.1 (4)
C4—O2—C5—O1178.4 (2)C1—C6—C7—N10.2 (2)
C4—O2—C5—C61.1 (3)C5—C6—C7—N1179.96 (18)
C2—C1—C6—C70.1 (2)C1—C6—C7—C3179.06 (19)
C9—C1—C6—C7177.9 (2)C5—C6—C7—C30.8 (3)
C2—C1—C6—C5179.7 (2)C4—C3—C7—N1179.6 (2)
C9—C1—C6—C52.2 (4)C4—C3—C7—C60.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10B···O1i0.962.463.404 (3)170
Symmetry code: (i) x1/2, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC10H11NO2
Mr177.20
Crystal system, space groupMonoclinic, P21/n
Temperature (K)295
a, b, c (Å)7.5556 (7), 8.4819 (8), 14.3081 (14)
β (°) 93.870 (6)
V3)914.86 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.33 × 0.28 × 0.15
Data collection
DiffractometerOxford Xcalibur Eos (Nova) CCD detector
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO RED; Oxford Diffraction, 2009)
Tmin, Tmax0.916, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
7291, 1692, 1176
Rint0.034
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.179, 1.18
No. of reflections1692
No. of parameters122
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.18

Computer programs: CrysAlis PRO CCD (Oxford Diffraction, 2009), CrysAlis PRO RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993), WinGX (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10B···O1i0.962.463.404 (3)170
Symmetry code: (i) x1/2, y+1/2, z1/2.
 

Acknowledgements

We thank the Department of Science and Technology, India, for use of the CCD facility set up under the IRHPA–DST program at IISc. We thank Professor T. N. Guru Row, IISc, Bangalore, for useful crystallographic discussions. FNK thanks the DST for Fast Track Proposal funding.

References

First citationAbid, O.-U.-R., Qadeer, G., Rama, N. H., Ruzicka, A. & Padelkova, Z. (2008). Acta Cryst. E64, o2018.  Web of Science CSD CrossRef IUCr Journals
First citationAbid, O., Rama, N. H., Qadeer, G., Khan, G. S. & Lu, X.-M. (2006). Acta Cryst. E62, o2895–o2896.  Web of Science CSD CrossRef IUCr Journals
First citationBarry, R. D. (1964). Chem. Rev. 64, 229–260.  CrossRef CAS Web of Science
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationHathwar, V. R., Manivel, P., Nawaz Khan, F. & Guru Row, T. N. (2007). Acta Cryst. E63, o3707.  Web of Science CSD CrossRef IUCr Journals
First citationOxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWatkin, D. J., Pearce, L. & Prout, C. K. (1993). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.

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