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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2196.
Published online 2009 August 22. doi:  10.1107/S1600536809032498
PMCID: PMC2969958

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

Abstract

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 [triangle]). For the synthesis of the reactant 3-methyl-1H-quinoxalin-2-one, see: Nikolaenko & Munro (2004 [triangle]).

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Object name is e-65-o2196-scheme1.jpg

Experimental

Crystal data

  • C12H10N2O
  • M r = 198.22
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2196-efi1.jpg
  • 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 [triangle]) T min = 0.985, T max = 0.991
  • 14275 measured reflections
  • 4058 independent reflections
  • 2428 reflections with I > 2σ(I)
  • R int = 0.046

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 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 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032498/xu2590sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032498/xu2590Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Experimental

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

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).

Figures

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.

Crystal data

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

Oxford Diffraction Xcalibur diffractometer4058 independent reflections
Radiation source: fine-focus sealed tube2428 reflections with I > 2σ(I)
graphiteRint = 0.046
ω and [var phi] scansθmax = 26.4°, θmin = 2.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)h = −22→26
Tmin = 0.985, Tmax = 0.991k = −5→5
14275 measured reflectionsl = −26→27

Refinement

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 = 0.97w = 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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)
H40.3427−0.41410.34600.043*
C50.24506 (10)−0.4804 (4)0.31742 (8)0.0438 (5)
H50.2459−0.61930.28480.053*
C60.18630 (10)−0.3990 (4)0.32887 (8)0.0441 (5)
H60.1466−0.48330.30380.053*
C70.18398 (8)−0.1987 (4)0.37573 (8)0.0342 (4)
H70.1430−0.14530.38300.041*
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)
H110.1331−0.23790.58570.043*
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)

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, °)

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—O1−1.0 (2)C21—N3—C13—O2−2.8 (2)
C8—N1—C1—C2−2.2 (2)C20—N3—C13—C14−3.2 (2)
C9—N1—C1—C2179.07 (12)C21—N3—C13—C14176.86 (13)
C3—N2—C2—C1−0.8 (2)C15—N4—C14—C130.6 (2)
C3—N2—C2—C12179.06 (15)C15—N4—C14—C24179.19 (15)
O1—C1—C2—N2−177.42 (15)O2—C13—C14—N4−178.51 (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—C12−177.34 (14)N3—C13—C14—C24−176.77 (15)
C2—N2—C3—C4179.21 (13)C14—N4—C15—C16178.69 (15)
C2—N2—C3—C8−1.3 (2)C14—N4—C15—C20−1.9 (2)
N2—C3—C4—C5179.55 (15)N4—C15—C16—C17−179.62 (15)
C8—C3—C4—C50.0 (2)C20—C15—C16—C170.9 (2)
C3—C4—C5—C6−0.1 (2)C15—C16—C17—C180.1 (3)
C4—C5—C6—C70.0 (3)C16—C17—C18—C19−0.8 (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—C7−178.59 (15)C13—N3—C20—C19−176.69 (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—C15−177.94 (13)
N2—C3—C8—C7−179.48 (14)N4—C15—C20—C19179.38 (14)
C4—C3—C8—C70.0 (2)C16—C15—C20—C19−1.2 (2)
N2—C3—C8—N11.6 (2)N4—C15—C20—N30.5 (2)
C4—C3—C8—N1−178.93 (13)C16—C15—C20—N3180.00 (14)
C1—N1—C9—C10−93.04 (17)C13—N3—C21—C22−107.74 (16)
C8—N1—C9—C1088.22 (17)C20—N3—C21—C2272.32 (18)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2590).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Benzeid, H., Vendier, L., Ramli, Y., Garrigues, B. & Essassi, E. M. (2008). Acta Cryst. E64, o2234. [PMC free article] [PubMed]
  • Nikolaenko, I. V. & Munro, O. Q. (2004). Acta Cryst. E60, o92–o94.
  • Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Abingdon, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography