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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2323.
Published online 2009 September 5. doi:  10.1107/S160053680903414X
PMCID: PMC2970207

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

Abstract

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

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

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Object name is e-65-o2323-scheme1.jpg

Experimental

Crystal data

  • C15H12N2O
  • M r = 236.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2323-efi1.jpg
  • a = 16.3919 (5) Å
  • b = 7.0775 (2) Å
  • c = 20.0214 (6) Å
  • β = 95.434 (2)°
  • V = 2312.32 (12) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 193 K
  • 0.60 × 0.20 × 0.10 mm

Data collection

  • Bruker APEX2 diffractometer
  • Absorption correction: none
  • 31360 measured reflections
  • 4682 independent reflections
  • 3068 reflections with I > 2σ(I)
  • R int = 0.054

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.114
  • S = 1.01
  • 4682 reflections
  • 327 parameters
  • H-atom parameters constrained
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; 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/S160053680903414X/sj2638sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903414X/sj2638Isup2.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

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

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).

Figures

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.

Crystal data

C15H12N2OF(000) = 992
Mr = 236.27Dx = 1.357 Mg m3
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 mm1
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

Bruker APEX2 diffractometer3068 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.054
graphiteθmax = 26.4°, θmin = 5.2°
[var phi] and ω scansh = −20→20
31360 measured reflectionsk = −8→8
4682 independent reflectionsl = −25→24

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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.00w = 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 Å3
0 restraintsΔρmin = −0.17 e Å3

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

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)

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, °)

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)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2638).

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]
  • Bruker (2005). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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