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

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ISSN: 2056-9890

3-Methyl-1-propargylquinoxalin-2(1H)-one

aLaboratoire de Chimie Organique Hétérocyclique, Pôle de compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, bLaboratoire de Chimie de Coordination, 205 Route de Narbonne, Toulouse Cedex 04, France, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 14 August 2009; accepted 16 August 2009; online 22 August 2009)

The ten-membered fused ring of the title compound, C12H10N2O, is essentially planar in the two independent mol­ecules of the asymmetric unit (r.m.s. deviations = 0.012 and 0.015 Å).

Related literature

For the crystal structure of 1-ethyl-3-methyl­quinoxalin-2(1H)-one, see: Benzeid et al. (2008[Benzeid, H., Vendier, L., Ramli, Y., Garrigues, B. & Essassi, E. M. (2008). Acta Cryst. E64, o2234.]). For the synthesis of the reactant 3-methyl-1H-quinoxalin-2-one, see: Nikolaenko & Munro (2004[Nikolaenko, I. V. & Munro, O. Q. (2004). Acta Cryst. E60, o92-o94.]).

[Scheme 1]

Experimental

Crystal data
  • C12H10N2O

  • Mr = 198.22

  • Monoclinic, P 21 /n

  • a = 21.124 (1) Å

  • b = 4.3709 (2) Å

  • c = 22.246 (1) Å

  • β = 105.354 (6)°

  • V = 1980.7 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 180 K

  • 0.20 × 0.15 × 0.08 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.985, Tmax = 0.991

  • 14275 measured reflections

  • 4058 independent reflections

  • 2428 reflections with I > 2σ(I)

  • Rint = 0.046

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.102

  • S = 0.97

  • 4058 reflections

  • 273 parameters

  • H-atom parameters constrained

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.22 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); data reduction: CrysAlis RED; 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

For the crystal structure of 1-ethyl-3-methylquinoxalin-2(1H)-one, see: Benzeid et al. (2008). For the synthesis of the reactant 3-methyl-1H-quinoxalin-2-one, see: Nikolaenko & Munro (2004).

Experimental top

To a solution of 3-methylquinoxalin-2(1H)-one (Nikolaenko & Munro et al., 2004) (1 g, 6.22 mmol) in DMF (20 ml) was added propargyl bromide (0.82 ml, 6.22 mmol), potassium carbonate (1 g, 7.46 mmol) and a catalytic quantity of tetra-n-butylammonium bromide. The mixture was stirred at room temperature for 24 h. The solution was filtered and the solvent removed under reduced pressure. The residue was recrystallized from ethanol to afford 3-methyl-1-(propargyl)quinoxalin-2(1H)-one as colorless crystals.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the two independent molecules of C12H10N2O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
3-Methyl-1-propargylquinoxalin-2(1H)-one top
Crystal data top
C12H10N2OF(000) = 832
Mr = 198.22Dx = 1.329 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5089 reflections
a = 21.124 (1) Åθ = 2.7–32.2°
b = 4.3709 (2) ŵ = 0.09 mm1
c = 22.246 (1) ÅT = 180 K
β = 105.354 (6)°Parallelepiped, yellow
V = 1980.7 (2) Å30.20 × 0.15 × 0.08 mm
Z = 8
Data collection top
Oxford Diffraction Xcalibur
diffractometer
4058 independent reflections
Radiation source: fine-focus sealed tube2428 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
ω and ϕ scansθmax = 26.4°, θmin = 2.8°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2006)
h = 2226
Tmin = 0.985, Tmax = 0.991k = 55
14275 measured reflectionsl = 2627
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0539P)2]
where P = (Fo2 + 2Fc2)/3
4058 reflections(Δ/σ)max = 0.001
273 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C12H10N2OV = 1980.7 (2) Å3
Mr = 198.22Z = 8
Monoclinic, P21/nMo Kα radiation
a = 21.124 (1) ŵ = 0.09 mm1
b = 4.3709 (2) ÅT = 180 K
c = 22.246 (1) Å0.20 × 0.15 × 0.08 mm
β = 105.354 (6)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer
4058 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2006)
2428 reflections with I > 2σ(I)
Tmin = 0.985, Tmax = 0.991Rint = 0.046
14275 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.102H-atom parameters constrained
S = 0.97Δρmax = 0.19 e Å3
4058 reflectionsΔρmin = 0.22 e Å3
273 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.30129 (6)0.4482 (3)0.53550 (5)0.0423 (3)
O20.53899 (5)0.4210 (3)0.84138 (5)0.0423 (3)
N10.24291 (6)0.1336 (3)0.46002 (5)0.0259 (3)
N20.36089 (6)0.0417 (3)0.43668 (6)0.0301 (3)
N30.45992 (6)0.5883 (3)0.75752 (6)0.0248 (3)
N40.40956 (6)0.9390 (3)0.83838 (6)0.0299 (3)
C10.30011 (8)0.2584 (4)0.49493 (7)0.0284 (4)
C20.36032 (8)0.1492 (4)0.48043 (7)0.0299 (4)
C30.30152 (8)0.1552 (4)0.40141 (7)0.0265 (4)
C40.30203 (9)0.3586 (4)0.35363 (7)0.0359 (4)
H40.34270.41410.34600.043*
C50.24506 (10)0.4804 (4)0.31742 (8)0.0438 (5)
H50.24590.61930.28480.053*
C60.18630 (10)0.3990 (4)0.32887 (8)0.0441 (5)
H60.14660.48330.30380.053*
C70.18398 (8)0.1987 (4)0.37573 (8)0.0342 (4)
H70.14300.14530.38300.041*
C80.24165 (8)0.0749 (3)0.41244 (7)0.0250 (4)
C90.18204 (8)0.2356 (4)0.47433 (8)0.0324 (4)
H9A0.18840.44600.49140.039*
H9B0.14620.24160.43530.039*
C100.16261 (7)0.0368 (4)0.51906 (7)0.0285 (4)
C110.14630 (8)0.1151 (4)0.55593 (8)0.0356 (4)
H110.13310.23790.58570.043*
C120.42291 (8)0.2734 (5)0.52009 (9)0.0484 (5)
H12A0.45940.20390.50400.073*
H12B0.42940.20060.56300.073*
H12C0.42120.49740.51940.073*
C130.49034 (7)0.5800 (4)0.81993 (7)0.0284 (4)
C140.46119 (8)0.7751 (4)0.85929 (7)0.0304 (4)
C150.37878 (7)0.9314 (4)0.77527 (7)0.0248 (4)
C160.32214 (7)1.1033 (4)0.75256 (8)0.0329 (4)
H160.30561.22410.78050.039*
C170.29004 (8)1.1009 (4)0.69069 (8)0.0365 (4)
H170.25141.21940.67560.044*
C180.31410 (8)0.9248 (4)0.64995 (8)0.0351 (4)
H180.29140.92130.60700.042*
C190.37008 (8)0.7558 (4)0.67064 (7)0.0294 (4)
H190.38630.63730.64220.035*
C200.40306 (7)0.7585 (3)0.73351 (7)0.0227 (3)
C210.48885 (8)0.4108 (4)0.71564 (7)0.0323 (4)
H21A0.52190.26770.74050.039*
H21B0.45410.28810.68720.039*
C220.52007 (8)0.6082 (4)0.67891 (8)0.0326 (4)
C230.54466 (9)0.7662 (5)0.64907 (8)0.0429 (5)
H230.56460.89450.62480.051*
C240.49583 (9)0.7818 (5)0.92679 (8)0.0503 (5)
H24A0.53810.88600.93280.075*
H24B0.50320.57190.94260.075*
H24C0.46900.89180.94950.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0525 (8)0.0439 (7)0.0306 (7)0.0029 (6)0.0113 (6)0.0077 (6)
O20.0237 (6)0.0535 (8)0.0453 (7)0.0048 (6)0.0016 (5)0.0074 (7)
N10.0248 (7)0.0277 (7)0.0275 (7)0.0052 (6)0.0108 (6)0.0035 (6)
N20.0285 (8)0.0303 (7)0.0341 (8)0.0050 (7)0.0130 (6)0.0079 (7)
N30.0218 (7)0.0273 (7)0.0259 (7)0.0017 (6)0.0076 (6)0.0022 (6)
N40.0257 (8)0.0407 (8)0.0237 (7)0.0059 (7)0.0074 (6)0.0041 (7)
C10.0349 (10)0.0295 (9)0.0216 (9)0.0026 (8)0.0089 (7)0.0055 (8)
C20.0287 (9)0.0295 (9)0.0304 (9)0.0024 (8)0.0056 (7)0.0078 (8)
C30.0319 (9)0.0251 (8)0.0248 (9)0.0068 (8)0.0118 (7)0.0082 (7)
C40.0519 (12)0.0287 (9)0.0323 (10)0.0102 (9)0.0202 (9)0.0063 (8)
C50.0722 (15)0.0324 (10)0.0271 (10)0.0005 (10)0.0133 (10)0.0017 (8)
C60.0542 (13)0.0368 (11)0.0324 (10)0.0058 (10)0.0041 (9)0.0046 (9)
C70.0323 (10)0.0330 (10)0.0341 (10)0.0008 (8)0.0035 (8)0.0089 (8)
C80.0309 (9)0.0223 (8)0.0228 (8)0.0040 (8)0.0089 (7)0.0061 (7)
C90.0301 (9)0.0324 (9)0.0394 (10)0.0100 (8)0.0173 (8)0.0052 (8)
C100.0227 (8)0.0355 (9)0.0285 (9)0.0043 (8)0.0086 (7)0.0034 (8)
C110.0274 (9)0.0492 (11)0.0323 (10)0.0023 (9)0.0115 (8)0.0025 (9)
C120.0335 (11)0.0510 (12)0.0554 (12)0.0012 (10)0.0023 (9)0.0028 (10)
C130.0192 (8)0.0364 (10)0.0276 (9)0.0079 (8)0.0028 (7)0.0023 (8)
C140.0250 (9)0.0424 (10)0.0236 (9)0.0082 (8)0.0064 (7)0.0001 (8)
C150.0211 (8)0.0293 (8)0.0251 (9)0.0075 (7)0.0083 (7)0.0020 (7)
C160.0255 (9)0.0325 (10)0.0429 (11)0.0003 (8)0.0130 (8)0.0012 (9)
C170.0232 (9)0.0396 (11)0.0440 (11)0.0002 (8)0.0041 (8)0.0103 (9)
C180.0316 (10)0.0416 (10)0.0286 (9)0.0087 (9)0.0017 (8)0.0076 (9)
C190.0289 (9)0.0354 (9)0.0237 (9)0.0068 (8)0.0067 (7)0.0012 (8)
C200.0177 (8)0.0248 (8)0.0253 (8)0.0055 (7)0.0052 (6)0.0010 (7)
C210.0355 (9)0.0298 (9)0.0347 (9)0.0001 (8)0.0144 (8)0.0050 (8)
C220.0273 (9)0.0364 (10)0.0374 (10)0.0010 (8)0.0144 (8)0.0074 (8)
C230.0389 (11)0.0477 (11)0.0493 (11)0.0020 (9)0.0244 (9)0.0007 (10)
C240.0372 (11)0.0816 (15)0.0279 (10)0.0060 (11)0.0014 (8)0.0031 (10)
Geometric parameters (Å, º) top
O1—C11.2213 (18)C9—H9B0.9900
O2—C131.2277 (18)C10—C111.176 (2)
N1—C11.365 (2)C11—H110.9500
N1—C81.3917 (19)C12—H12A0.9800
N1—C91.4732 (19)C12—H12B0.9800
N2—C21.285 (2)C12—H12C0.9800
N2—C31.383 (2)C13—C141.469 (2)
N3—C131.3673 (19)C14—C241.486 (2)
N3—C201.3934 (19)C15—C161.390 (2)
N3—C211.4643 (19)C15—C201.396 (2)
N4—C141.285 (2)C16—C171.364 (2)
N4—C151.3826 (18)C16—H160.9500
C1—C21.472 (2)C17—C181.384 (2)
C2—C121.484 (2)C17—H170.9500
C3—C41.388 (2)C18—C191.367 (2)
C3—C81.395 (2)C18—H180.9500
C4—C51.367 (2)C19—C201.388 (2)
C4—H40.9500C19—H190.9500
C5—C61.378 (3)C21—C221.460 (2)
C5—H50.9500C21—H21A0.9900
C6—C71.372 (2)C21—H21B0.9900
C6—H60.9500C22—C231.171 (2)
C7—C81.385 (2)C23—H230.9500
C7—H70.9500C24—H24A0.9800
C9—C101.459 (2)C24—H24B0.9800
C9—H9A0.9900C24—H24C0.9800
C1—N1—C8122.01 (13)H12A—C12—H12B109.5
C1—N1—C9116.60 (13)C2—C12—H12C109.5
C8—N1—C9121.38 (13)H12A—C12—H12C109.5
C2—N2—C3118.28 (14)H12B—C12—H12C109.5
C13—N3—C20121.95 (13)O2—C13—N3121.98 (15)
C13—N3—C21117.96 (13)O2—C13—C14122.47 (15)
C20—N3—C21120.10 (13)N3—C13—C14115.55 (14)
C14—N4—C15118.69 (14)N4—C14—C13123.89 (15)
O1—C1—N1122.25 (15)N4—C14—C24119.90 (16)
O1—C1—C2122.16 (16)C13—C14—C24116.20 (15)
N1—C1—C2115.59 (14)N4—C15—C16118.96 (14)
N2—C2—C1123.96 (15)N4—C15—C20122.13 (14)
N2—C2—C12120.14 (15)C16—C15—C20118.91 (14)
C1—C2—C12115.90 (15)C17—C16—C15120.85 (16)
N2—C3—C4118.32 (15)C17—C16—H16119.6
N2—C3—C8122.53 (14)C15—C16—H16119.6
C4—C3—C8119.15 (16)C16—C17—C18119.63 (16)
C5—C4—C3121.12 (17)C16—C17—H17120.2
C5—C4—H4119.4C18—C17—H17120.2
C3—C4—H4119.4C19—C18—C17120.99 (16)
C4—C5—C6119.08 (17)C19—C18—H18119.5
C4—C5—H5120.5C17—C18—H18119.5
C6—C5—H5120.5C18—C19—C20119.59 (16)
C7—C6—C5121.35 (17)C18—C19—H19120.2
C7—C6—H6119.3C20—C19—H19120.2
C5—C6—H6119.3C19—C20—N3122.26 (14)
C6—C7—C8119.64 (17)C19—C20—C15120.01 (14)
C6—C7—H7120.2N3—C20—C15117.72 (13)
C8—C7—H7120.2C22—C21—N3111.69 (13)
C7—C8—N1122.76 (14)C22—C21—H21A109.3
C7—C8—C3119.66 (15)N3—C21—H21A109.3
N1—C8—C3117.57 (14)C22—C21—H21B109.3
C10—C9—N1112.71 (13)N3—C21—H21B109.3
C10—C9—H9A109.1H21A—C21—H21B107.9
N1—C9—H9A109.1C23—C22—C21179.5 (2)
C10—C9—H9B109.1C22—C23—H23180.0
N1—C9—H9B109.1C14—C24—H24A109.5
H9A—C9—H9B107.8C14—C24—H24B109.5
C11—C10—C9177.82 (17)H24A—C24—H24B109.5
C10—C11—H11180.0C14—C24—H24C109.5
C2—C12—H12A109.5H24A—C24—H24C109.5
C2—C12—H12B109.5H24B—C24—H24C109.5
C8—N1—C1—O1177.78 (14)C20—N3—C13—O2177.17 (14)
C9—N1—C1—O11.0 (2)C21—N3—C13—O22.8 (2)
C8—N1—C1—C22.2 (2)C20—N3—C13—C143.2 (2)
C9—N1—C1—C2179.07 (12)C21—N3—C13—C14176.86 (13)
C3—N2—C2—C10.8 (2)C15—N4—C14—C130.6 (2)
C3—N2—C2—C12179.06 (15)C15—N4—C14—C24179.19 (15)
O1—C1—C2—N2177.42 (15)O2—C13—C14—N4178.51 (16)
N1—C1—C2—N22.6 (2)N3—C13—C14—N41.9 (2)
O1—C1—C2—C122.7 (2)O2—C13—C14—C242.9 (2)
N1—C1—C2—C12177.34 (14)N3—C13—C14—C24176.77 (15)
C2—N2—C3—C4179.21 (13)C14—N4—C15—C16178.69 (15)
C2—N2—C3—C81.3 (2)C14—N4—C15—C201.9 (2)
N2—C3—C4—C5179.55 (15)N4—C15—C16—C17179.62 (15)
C8—C3—C4—C50.0 (2)C20—C15—C16—C170.9 (2)
C3—C4—C5—C60.1 (2)C15—C16—C17—C180.1 (3)
C4—C5—C6—C70.0 (3)C16—C17—C18—C190.8 (3)
C5—C6—C7—C80.0 (2)C17—C18—C19—C200.6 (2)
C6—C7—C8—N1178.84 (14)C18—C19—C20—N3179.23 (14)
C6—C7—C8—C30.0 (2)C18—C19—C20—C150.4 (2)
C1—N1—C8—C7178.59 (15)C13—N3—C20—C19176.69 (14)
C9—N1—C8—C70.1 (2)C21—N3—C20—C193.2 (2)
C1—N1—C8—C30.3 (2)C13—N3—C20—C152.1 (2)
C9—N1—C8—C3178.99 (13)C21—N3—C20—C15177.94 (13)
N2—C3—C8—C7179.48 (14)N4—C15—C20—C19179.38 (14)
C4—C3—C8—C70.0 (2)C16—C15—C20—C191.2 (2)
N2—C3—C8—N11.6 (2)N4—C15—C20—N30.5 (2)
C4—C3—C8—N1178.93 (13)C16—C15—C20—N3180.00 (14)
C1—N1—C9—C1093.04 (17)C13—N3—C21—C22107.74 (16)
C8—N1—C9—C1088.22 (17)C20—N3—C21—C2272.32 (18)

Experimental details

Crystal data
Chemical formulaC12H10N2O
Mr198.22
Crystal system, space groupMonoclinic, P21/n
Temperature (K)180
a, b, c (Å)21.124 (1), 4.3709 (2), 22.246 (1)
β (°) 105.354 (6)
V3)1980.7 (2)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.20 × 0.15 × 0.08
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2006)
Tmin, Tmax0.985, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
14275, 4058, 2428
Rint0.046
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.102, 0.97
No. of reflections4058
No. of parameters273
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.22

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

 

Acknowledgements

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

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