supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

Acta Cryst. (2009). E65, o2323    [ doi:10.1107/S160053680903414X ]

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

H. Benzeid, E. M. Essassi, N. Saffon, B. Garrigues and S. W. Ng

Abstract top

The phenyl substituents in both independent molecules of the title compound, C15H12N2O, are twisted with respect to the quinoxaline system [dihedral angles = 19.3 (1) and 30.4 (1)°].

Related literature top

For the structure of 1-ethyl-3-methylquinoxalin-2(1H)-one, see: Benzeid et al. (2008).

Experimental top

3-Phenylquinoxalin-2(1H)-one (1 g, 4.5 mmol), methyl iodide (0.31 ml, 5.0 mmol), potassium carbonate (0.7 g, 5.0 mmol) and a catalytic quantity of tetra-n-butylammonium bromide were stirred in N,N-dimethylformamide (20 ml) for 24 h. The mixture was filtered to remove the salts and the solvent removed under reduce pressure. The residue was recrystallized in ethanol to afford the pure compound in 80% yield.The formulation was established by proton and carbon-13 NMR spectroscopy in CDCl3.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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. A thermal ellipsoid plot (Barbour, 2001) of the two unique molecules of C15H16N2O2 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
1-Methyl-3-phenylquinoxalin-2(1H)-one top
Crystal data top
C15H12N2OF(000) = 992
Mr = 236.27Dx = 1.357 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4338 reflections
a = 16.3919 (5) Åθ = 2.5–24.9°
b = 7.0775 (2) ŵ = 0.09 mm−1
c = 20.0214 (6) ÅT = 193 K
β = 95.434 (2)°Plate, yellow
V = 2312.32 (12) Å30.60 × 0.20 × 0.10 mm
Z = 8
Data collection top
Bruker APEX2
diffractometer		3068 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.054
graphiteθmax = 26.4°, θmin = 5.2°
φ and ω scansh = −20→20
31360 measured reflectionsk = −8→8
4682 independent reflectionsl = −25→24
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0498P)2 + 0.4004P]
where P = (Fo2 + 2Fc2)/3
4682 reflections(Δ/σ)max = 0.001
327 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.17 e Å−3
Crystal data top
C15H12N2OV = 2312.32 (12) Å3
Mr = 236.27Z = 8
Monoclinic, P21/nMo Kα radiation
a = 16.3919 (5) ŵ = 0.09 mm−1
b = 7.0775 (2) ÅT = 193 K
c = 20.0214 (6) Å0.60 × 0.20 × 0.10 mm
β = 95.434 (2)°
Data collection top
Bruker APEX2
diffractometer		Rint = 0.054
31360 measured reflectionsθmax = 26.4°
4682 independent reflectionsStandard reflections: 0
3068 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.114Δρmax = 0.23 e Å−3
S = 1.00Δρmin = −0.17 e Å−3
4682 reflectionsAbsolute structure: ?
327 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.53417 (7)0.34744 (19)0.19948 (6)0.0472 (4)
O20.62711 (8)0.8355 (2)0.09382 (7)0.0632 (4)
N10.42018 (8)0.3190 (2)0.12599 (7)0.0323 (3)
N20.33162 (8)0.2202 (2)0.23283 (6)0.0326 (3)
N30.69753 (8)0.8664 (2)0.19620 (7)0.0358 (4)
N40.54955 (8)0.86008 (19)0.25385 (7)0.0317 (3)
C10.46011 (10)0.3149 (2)0.18965 (9)0.0331 (4)
C20.40856 (10)0.2669 (2)0.24408 (8)0.0300 (4)
C30.44373 (10)0.2670 (2)0.31523 (8)0.0309 (4)
C40.50477 (10)0.3928 (3)0.34009 (9)0.0389 (4)
H40.52810.47790.31050.047*
C50.53143 (11)0.3938 (3)0.40790 (9)0.0435 (5)
H50.57280.48020.42460.052*
C60.49836 (11)0.2705 (3)0.45122 (9)0.0453 (5)
H60.51690.27220.49760.054*
C70.43825 (11)0.1445 (3)0.42723 (9)0.0418 (5)
H70.41570.05900.45710.050*
C80.41091 (10)0.1428 (2)0.35977 (8)0.0364 (4)
H80.36940.05620.34350.044*
C90.46906 (12)0.3662 (3)0.07079 (9)0.0464 (5)
H9A0.45070.48760.05120.070*
H9B0.46220.26740.03640.070*
H9C0.52700.37510.08780.070*
C100.33732 (10)0.2762 (2)0.11315 (8)0.0306 (4)
C110.29496 (10)0.2221 (2)0.16767 (8)0.0309 (4)
C120.21273 (10)0.1659 (3)0.15667 (9)0.0382 (4)
H120.18440.12590.19350.046*
C130.17287 (11)0.1683 (3)0.09346 (9)0.0428 (5)
H130.11730.12910.08620.051*
C140.21443 (12)0.2287 (3)0.03988 (9)0.0438 (5)
H140.18630.2334−0.00380.053*
C150.29569 (11)0.2818 (2)0.04900 (8)0.0380 (4)
H150.32320.32210.01180.046*
C160.62597 (11)0.8499 (3)0.15482 (9)0.0382 (4)
C170.54917 (10)0.8488 (2)0.18917 (8)0.0309 (4)
C180.46772 (10)0.8295 (2)0.14974 (8)0.0312 (4)
C190.45321 (12)0.8707 (3)0.08144 (9)0.0407 (4)
H190.49690.91370.05730.049*
C200.37535 (13)0.8491 (3)0.04856 (10)0.0472 (5)
H200.36610.87800.00210.057*
C210.31130 (12)0.7860 (3)0.08274 (10)0.0469 (5)
H210.25840.76940.05970.056*
C220.32428 (11)0.7471 (3)0.15040 (10)0.0441 (5)
H220.28020.70510.17420.053*
C230.40153 (10)0.7693 (2)0.18359 (9)0.0369 (4)
H230.40980.74320.23030.044*
C240.77511 (11)0.8735 (3)0.16470 (10)0.0487 (5)
H24A0.76350.86990.11580.073*
H24B0.80910.76470.17950.073*
H24C0.80430.99050.17780.073*
C250.69876 (10)0.8736 (2)0.26575 (9)0.0341 (4)
C260.62318 (10)0.8714 (2)0.29362 (8)0.0314 (4)
C270.62170 (11)0.8786 (3)0.36323 (9)0.0402 (4)
H270.57070.87920.38210.048*
C280.69355 (12)0.8848 (3)0.40451 (10)0.0479 (5)
H280.69230.88900.45180.057*
C290.76810 (12)0.8850 (3)0.37677 (10)0.0499 (5)
H290.81760.88850.40550.060*
C300.77140 (11)0.8802 (3)0.30840 (10)0.0437 (5)
H300.82290.88130.29020.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0283 (7)0.0654 (9)0.0483 (8)−0.0051 (6)0.0063 (6)−0.0005 (7)
O20.0531 (9)0.1003 (13)0.0387 (8)0.0090 (8)0.0178 (7)−0.0003 (8)
N10.0342 (8)0.0341 (8)0.0294 (8)−0.0007 (6)0.0075 (6)−0.0014 (6)
N20.0297 (8)0.0389 (8)0.0288 (8)−0.0005 (7)0.0010 (6)−0.0027 (6)
N30.0315 (8)0.0342 (8)0.0439 (9)0.0005 (7)0.0150 (7)−0.0008 (7)
N40.0310 (7)0.0315 (8)0.0330 (8)0.0001 (6)0.0052 (6)−0.0016 (6)
C10.0288 (9)0.0313 (9)0.0396 (10)0.0018 (7)0.0047 (8)−0.0034 (8)
C20.0278 (9)0.0288 (9)0.0334 (9)0.0018 (7)0.0023 (7)−0.0033 (7)
C30.0241 (8)0.0348 (9)0.0334 (9)0.0041 (7)0.0007 (7)−0.0022 (8)
C40.0324 (9)0.0425 (11)0.0415 (11)0.0004 (8)0.0018 (8)−0.0024 (8)
C50.0340 (10)0.0506 (12)0.0439 (11)0.0010 (9)−0.0061 (8)−0.0103 (9)
C60.0403 (11)0.0583 (13)0.0354 (10)0.0099 (10)−0.0061 (8)−0.0055 (10)
C70.0387 (10)0.0496 (12)0.0366 (10)0.0058 (9)0.0004 (8)0.0066 (9)
C80.0311 (9)0.0396 (10)0.0376 (10)−0.0010 (8)−0.0009 (8)0.0008 (8)
C90.0509 (11)0.0492 (12)0.0417 (11)−0.0096 (10)0.0174 (9)−0.0008 (9)
C100.0336 (9)0.0266 (9)0.0315 (9)0.0030 (7)0.0029 (7)−0.0033 (7)
C110.0303 (9)0.0321 (9)0.0298 (9)0.0032 (7)0.0014 (7)−0.0035 (7)
C120.0308 (9)0.0485 (11)0.0350 (10)0.0004 (8)0.0015 (8)−0.0013 (8)
C130.0319 (10)0.0520 (12)0.0427 (11)0.0014 (9)−0.0059 (8)−0.0030 (9)
C140.0457 (11)0.0479 (12)0.0353 (10)0.0051 (9)−0.0089 (9)−0.0018 (9)
C150.0479 (11)0.0362 (10)0.0300 (9)0.0010 (9)0.0036 (8)0.0008 (8)
C160.0401 (10)0.0398 (11)0.0361 (10)0.0026 (8)0.0110 (8)0.0025 (8)
C170.0362 (9)0.0241 (9)0.0332 (10)0.0025 (7)0.0082 (7)−0.0006 (7)
C180.0353 (9)0.0259 (9)0.0326 (9)0.0056 (7)0.0045 (7)−0.0030 (7)
C190.0489 (11)0.0371 (10)0.0363 (10)0.0060 (9)0.0046 (9)−0.0018 (8)
C200.0572 (13)0.0453 (12)0.0367 (10)0.0127 (10)−0.0077 (10)−0.0053 (9)
C210.0431 (11)0.0407 (11)0.0538 (13)0.0071 (9)−0.0109 (10)−0.0133 (9)
C220.0370 (10)0.0414 (11)0.0533 (12)−0.0002 (9)0.0004 (9)−0.0040 (9)
C230.0359 (10)0.0364 (10)0.0381 (10)0.0020 (8)0.0017 (8)−0.0015 (8)
C240.0368 (10)0.0467 (12)0.0666 (13)−0.0015 (9)0.0262 (10)−0.0030 (10)
C250.0331 (9)0.0252 (9)0.0445 (10)0.0003 (7)0.0066 (8)−0.0002 (8)
C260.0293 (9)0.0280 (9)0.0372 (10)0.0016 (7)0.0044 (7)−0.0008 (7)
C270.0383 (10)0.0439 (11)0.0384 (10)0.0012 (9)0.0040 (8)−0.0013 (8)
C280.0502 (12)0.0499 (12)0.0417 (11)0.0009 (10)−0.0058 (9)−0.0030 (9)
C290.0405 (11)0.0478 (12)0.0582 (13)0.0006 (9)−0.0116 (10)−0.0024 (10)
C300.0301 (10)0.0380 (11)0.0631 (13)−0.0019 (8)0.0049 (9)−0.0008 (9)
Geometric parameters (Å, °) top
O1—C11.2331 (19)C12—H120.9500
O2—C161.228 (2)C13—C141.391 (3)
N1—C11.377 (2)C13—H130.9500
N1—C101.392 (2)C14—C151.380 (2)
N1—C91.464 (2)C14—H140.9500
N2—C21.3027 (19)C15—H150.9500
N2—C111.384 (2)C16—C171.491 (2)
N3—C161.376 (2)C17—C181.491 (2)
N3—C251.392 (2)C18—C191.396 (2)
N3—C241.473 (2)C18—C231.399 (2)
N4—C171.297 (2)C19—C201.388 (3)
N4—C261.384 (2)C19—H190.9500
C1—C21.480 (2)C20—C211.381 (3)
C2—C31.485 (2)C20—H200.9500
C3—C41.395 (2)C21—C221.379 (3)
C3—C81.396 (2)C21—H210.9500
C4—C51.386 (2)C22—C231.382 (2)
C4—H40.9500C22—H220.9500
C5—C61.377 (3)C23—H230.9500
C5—H50.9500C24—H24A0.9800
C6—C71.381 (3)C24—H24B0.9800
C6—H60.9500C24—H24C0.9800
C7—C81.382 (2)C25—C301.399 (2)
C7—H70.9500C25—C261.406 (2)
C8—H80.9500C26—C271.397 (2)
C9—H9A0.9800C27—C281.374 (2)
C9—H9B0.9800C27—H270.9500
C9—H9C0.9800C28—C291.389 (3)
C10—C151.397 (2)C28—H280.9500
C10—C111.401 (2)C29—C301.376 (3)
C11—C121.402 (2)C29—H290.9500
C12—C131.368 (2)C30—H300.9500
C1—N1—C10122.44 (14)C13—C14—H14119.4
C1—N1—C9117.23 (14)C14—C15—C10119.70 (17)
C10—N1—C9120.31 (14)C14—C15—H15120.1
C2—N2—C11119.18 (14)C10—C15—H15120.1
C16—N3—C25122.45 (14)O2—C16—N3120.92 (16)
C16—N3—C24117.81 (15)O2—C16—C17123.49 (16)
C25—N3—C24119.73 (15)N3—C16—C17115.58 (15)
C17—N4—C26119.98 (14)N4—C17—C16122.41 (15)
O1—C1—N1121.22 (15)N4—C17—C18116.98 (15)
O1—C1—C2123.17 (16)C16—C17—C18120.59 (15)
N1—C1—C2115.60 (14)C19—C18—C23118.03 (16)
N2—C2—C1122.79 (15)C19—C18—C17124.07 (16)
N2—C2—C3116.58 (14)C23—C18—C17117.89 (15)
C1—C2—C3120.62 (14)C20—C19—C18120.34 (18)
C4—C3—C8118.73 (15)C20—C19—H19119.8
C4—C3—C2122.86 (15)C18—C19—H19119.8
C8—C3—C2118.31 (15)C21—C20—C19120.59 (18)
C5—C4—C3120.11 (17)C21—C20—H20119.7
C5—C4—H4119.9C19—C20—H20119.7
C3—C4—H4119.9C22—C21—C20119.84 (18)
C6—C5—C4120.47 (18)C22—C21—H21120.1
C6—C5—H5119.8C20—C21—H21120.1
C4—C5—H5119.8C21—C22—C23119.92 (19)
C5—C6—C7120.04 (17)C21—C22—H22120.0
C5—C6—H6120.0C23—C22—H22120.0
C7—C6—H6120.0C22—C23—C18121.26 (17)
C6—C7—C8120.00 (18)C22—C23—H23119.4
C6—C7—H7120.0C18—C23—H23119.4
C8—C7—H7120.0N3—C24—H24A109.5
C7—C8—C3120.65 (16)N3—C24—H24B109.5
C7—C8—H8119.7H24A—C24—H24B109.5
C3—C8—H8119.7N3—C24—H24C109.5
N1—C9—H9A109.5H24A—C24—H24C109.5
N1—C9—H9B109.5H24B—C24—H24C109.5
H9A—C9—H9B109.5N3—C25—C30122.88 (16)
N1—C9—H9C109.5N3—C25—C26117.83 (15)
H9A—C9—H9C109.5C30—C25—C26119.28 (17)
H9B—C9—H9C109.5N4—C26—C27118.65 (15)
N1—C10—C15123.16 (15)N4—C26—C25121.70 (15)
N1—C10—C11117.56 (14)C27—C26—C25119.65 (16)
C15—C10—C11119.28 (16)C28—C27—C26120.42 (17)
N2—C11—C10122.27 (15)C28—C27—H27119.8
N2—C11—C12118.07 (15)C26—C27—H27119.8
C10—C11—C12119.66 (15)C27—C28—C29119.73 (18)
C13—C12—C11120.63 (17)C27—C28—H28120.1
C13—C12—H12119.7C29—C28—H28120.1
C11—C12—H12119.7C30—C29—C28121.12 (18)
C12—C13—C14119.40 (17)C30—C29—H29119.4
C12—C13—H13120.3C28—C29—H29119.4
C14—C13—H13120.3C29—C30—C25119.79 (17)
C15—C14—C13121.25 (17)C29—C30—H30120.1
C15—C14—H14119.4C25—C30—H30120.1
C10—N1—C1—O1177.65 (15)C25—N3—C16—O2−176.73 (17)
C9—N1—C1—O1−0.8 (2)C24—N3—C16—O22.3 (3)
C10—N1—C1—C2−1.6 (2)C25—N3—C16—C172.6 (2)
C9—N1—C1—C2179.90 (15)C24—N3—C16—C17−178.34 (15)
C11—N2—C2—C1−2.6 (2)C26—N4—C17—C16−0.8 (2)
C11—N2—C2—C3178.43 (14)C26—N4—C17—C18177.68 (14)
O1—C1—C2—N2−175.20 (16)O2—C16—C17—N4178.43 (17)
N1—C1—C2—N24.1 (2)N3—C16—C17—N4−0.9 (2)
O1—C1—C2—C33.7 (3)O2—C16—C17—C180.0 (3)
N1—C1—C2—C3−177.04 (14)N3—C16—C17—C18−179.32 (14)
N2—C2—C3—C4−147.10 (16)N4—C17—C18—C19160.36 (16)
C1—C2—C3—C433.9 (2)C16—C17—C18—C19−21.2 (2)
N2—C2—C3—C829.2 (2)N4—C17—C18—C23−18.6 (2)
C1—C2—C3—C8−149.75 (16)C16—C17—C18—C23159.91 (15)
C8—C3—C4—C5−0.4 (3)C23—C18—C19—C20−0.9 (2)
C2—C3—C4—C5175.90 (16)C17—C18—C19—C20−179.88 (16)
C3—C4—C5—C60.3 (3)C18—C19—C20—C21−0.3 (3)
C4—C5—C6—C70.1 (3)C19—C20—C21—C221.2 (3)
C5—C6—C7—C8−0.4 (3)C20—C21—C22—C23−0.8 (3)
C6—C7—C8—C30.3 (3)C21—C22—C23—C18−0.5 (3)
C4—C3—C8—C70.1 (3)C19—C18—C23—C221.3 (3)
C2—C3—C8—C7−176.37 (15)C17—C18—C23—C22−179.67 (15)
C1—N1—C10—C15179.25 (15)C16—N3—C25—C30176.49 (16)
C9—N1—C10—C15−2.3 (2)C24—N3—C25—C30−2.5 (2)
C1—N1—C10—C11−1.9 (2)C16—N3—C25—C26−2.6 (2)
C9—N1—C10—C11176.53 (15)C24—N3—C25—C26178.38 (15)
C2—N2—C11—C10−1.3 (2)C17—N4—C26—C27−178.43 (16)
C2—N2—C11—C12178.21 (15)C17—N4—C26—C250.9 (2)
N1—C10—C11—N23.5 (2)N3—C25—C26—N40.8 (2)
C15—C10—C11—N2−177.55 (15)C30—C25—C26—N4−178.34 (15)
N1—C10—C11—C12−175.94 (15)N3—C25—C26—C27−179.93 (16)
C15—C10—C11—C123.0 (2)C30—C25—C26—C270.9 (2)
N2—C11—C12—C13178.77 (16)N4—C26—C27—C28178.28 (16)
C10—C11—C12—C13−1.7 (3)C25—C26—C27—C28−1.0 (3)
C11—C12—C13—C14−0.6 (3)C26—C27—C28—C290.4 (3)
C12—C13—C14—C151.6 (3)C27—C28—C29—C300.4 (3)
C13—C14—C15—C10−0.3 (3)C28—C29—C30—C25−0.5 (3)
N1—C10—C15—C14176.88 (16)N3—C25—C30—C29−179.29 (17)
C11—C10—C15—C14−2.0 (2)C26—C25—C30—C29−0.2 (3)
Acknowledgements top

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

references
References top

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.

Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2009). publCIF. In preparation.