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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1821.
Published online 2008 August 23. doi:  10.1107/S1600536808026810
PMCID: PMC2960597

Quinoxalin-2-yl o-tolyl ether

Abstract

The dihedral angle between the two aromatic ring systems in the title compound, C15H12N2O, is 85.9 (1)°; The angle at the O atom is widened to 118.2 (2)°. The quinoxalin­yloxy part of the mol­ecule lies on a mirror plane and the tolyl group is disordered over two positions about the mirror plane.

Related literature

The title compound exhibits fluorescence; see: Abdullah (2005 [triangle]); Kawai et al. (2001 [triangle]); Mohd Salleh et al. (2007 [triangle]).

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Object name is e-64-o1821-scheme1.jpg

Experimental

Crystal data

  • C15H12N2O
  • M r = 236.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1821-efi1.jpg
  • a = 7.874 (2) Å
  • b = 7.413 (1) Å
  • c = 10.596 (2) Å
  • β = 108.332 (3)°
  • V = 587.1 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 (2) K
  • 0.20 × 0.20 × 0.08 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 3392 measured reflections
  • 1443 independent reflections
  • 1032 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.065
  • wR(F 2) = 0.183
  • S = 1.03
  • 1443 reflections
  • 119 parameters
  • H-atom parameters constrained
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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, 2008 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026810/bt2769sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026810/bt2769Isup2.hkl

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

Acknowledgments

We thank the University of Malaya for supporting this study (grant No. F2358/2008 A).

supplementary crystallographic information

Comment

(type here to add)

Experimental

o-Cresol (0.54 g, 5 mmol) was dissolved in a small volume of water containing potassium hydroxide (0.20 g, 5 mmol). The mixture was heated to remove the water to give a brown compound. The compound and 2-chloroquinoxaline (0.82, g, 5 mmol) were heated in THF (15 ml) for 8 h. The mixture was in 1 N sodium hydroxide; the aqueous solution was extracted with dichloromethane. The organic phase was dried over sodium sulfate. Evaporation of the solvent gave a yellow product, which was was washed with chloroform to remove impurities. Crystals were obtained upon recrystallization from an ethyl acetate/hexane mixture.

Refinement

The tolyl group is disordered about a mirror plane; the phenylene ring was refined as a rigid hexagon. The seven carbon atoms were allowed to refine off the symmetry element; the atoms were all given 0.5 site occupancy.

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

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C15H12N2O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C15H12N2OF000 = 248
Mr = 236.27Dx = 1.337 Mg m3
Monoclinic, P21/mMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybCell parameters from 756 reflections
a = 7.874 (2) Åθ = 2.7–24.6º
b = 7.413 (1) ŵ = 0.09 mm1
c = 10.596 (2) ÅT = 100 (2) K
β = 108.332 (3)ºBlock, colorless
V = 587.1 (2) Å30.20 × 0.20 × 0.08 mm
Z = 2

Data collection

Bruker SMART APEX diffractometer1032 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
Monochromator: graphiteθmax = 27.5º
T = 100(2) Kθmin = 2.0º
ω scansh = −10→8
Absorption correction: Nonek = −9→8
3392 measured reflectionsl = −12→13
1443 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.065H-atom parameters constrained
wR(F2) = 0.183  w = 1/[σ2(Fo2) + (0.0776P)2 + 0.4106P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
1443 reflectionsΔρmax = 0.24 e Å3
119 parametersΔρmin = −0.31 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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

xyzUiso*/UeqOcc. (<1)
O10.1778 (2)0.25000.64890 (18)0.0405 (6)
N10.4752 (3)0.25000.7791 (2)0.0552 (9)
N20.3518 (3)0.25000.9997 (2)0.0479 (8)
C10.2266 (3)0.1943 (3)0.5368 (2)0.0256 (8)0.50
C20.2256 (5)0.0171 (3)0.4936 (3)0.047 (2)0.50
H20.2002−0.07870.54450.056*0.50
C30.2619 (5)−0.0199 (3)0.3761 (3)0.0473 (11)0.50
H30.2612−0.14100.34660.057*0.50
C40.2991 (4)0.1203 (4)0.3017 (2)0.0417 (12)0.50
H40.32390.09500.22130.050*0.50
C50.3000 (3)0.2975 (3)0.3449 (2)0.0345 (15)0.50
H50.32550.39330.29400.041*0.50
C60.2638 (3)0.3345 (3)0.4624 (3)0.0313 (8)0.50
C70.2599 (11)0.5228 (12)0.5056 (7)0.0496 (17)0.50
H7A0.34490.59460.47610.074*0.50
H7B0.29320.52720.60280.074*0.50
H7C0.13910.57190.46660.074*0.50
C80.3083 (3)0.25000.7686 (2)0.0300 (6)
C90.2449 (4)0.25000.8784 (3)0.0393 (8)
H90.11940.25000.86330.047*
C100.5314 (3)0.25001.0167 (2)0.0284 (6)
C110.6553 (4)0.25001.1448 (3)0.0429 (8)
H110.61350.25001.21970.051*
C120.8343 (4)0.25001.1638 (3)0.0398 (8)
H120.91690.25001.25130.048*
C130.8952 (4)0.25001.0547 (3)0.0631 (12)
H131.02010.25001.06740.076*
C140.7769 (4)0.25000.9289 (3)0.0889 (19)
H140.82090.25000.85510.107*
C150.5922 (3)0.25000.9066 (3)0.0378 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0199 (9)0.0771 (16)0.0236 (9)0.0000.0055 (7)0.000
N10.0196 (11)0.123 (3)0.0224 (12)0.0000.0065 (9)0.000
N20.0248 (12)0.093 (2)0.0270 (12)0.0000.0090 (9)0.000
C10.0198 (14)0.033 (2)0.0229 (16)0.0038 (12)0.0051 (12)0.0008 (12)
C20.057 (4)0.056 (5)0.031 (3)0.004 (3)0.018 (3)0.002 (3)
C30.072 (3)0.041 (3)0.032 (2)0.015 (2)0.021 (2)0.0047 (19)
C40.040 (2)0.064 (4)0.024 (2)0.015 (2)0.0142 (17)0.002 (2)
C50.0231 (15)0.054 (5)0.0263 (17)−0.0015 (15)0.0075 (13)0.0121 (16)
C60.0175 (15)0.0301 (19)0.039 (2)−0.0008 (15)−0.0015 (15)0.0020 (17)
C70.055 (3)0.037 (3)0.054 (4)−0.001 (3)0.013 (3)0.008 (3)
C80.0220 (12)0.0435 (16)0.0233 (12)0.0000.0053 (10)0.000
C90.0188 (12)0.069 (2)0.0304 (14)0.0000.0084 (11)0.000
C100.0230 (12)0.0369 (15)0.0259 (13)0.0000.0086 (10)0.000
C110.0303 (14)0.076 (2)0.0227 (13)0.0000.0093 (11)0.000
C120.0265 (14)0.065 (2)0.0243 (13)0.0000.0020 (11)0.000
C130.0211 (14)0.137 (4)0.0291 (15)0.0000.0053 (12)0.000
C140.0238 (15)0.221 (6)0.0247 (16)0.0000.0111 (13)0.000
C150.0218 (13)0.067 (2)0.0236 (13)0.0000.0063 (10)0.000

Geometric parameters (Å, °)

O1—C81.359 (3)C6—C71.472 (9)
O1—C11.420 (3)C7—H7A0.9800
O1—C1i1.420 (3)C7—H7B0.9800
N1—C81.283 (3)C7—H7C0.9800
N1—C151.375 (3)C8—C91.402 (4)
N2—C91.296 (4)C9—H90.9500
N2—C101.369 (3)C10—C151.392 (4)
C1—C21.3900C10—C111.400 (4)
C1—C61.3900C11—C121.360 (4)
C2—C31.3900C11—H110.9500
C2—H20.9500C12—C131.384 (4)
C3—C41.3900C12—H120.9500
C3—H30.9500C13—C141.365 (4)
C4—C51.3900C13—H130.9500
C4—H40.9500C14—C151.398 (4)
C5—C61.3900C14—H140.9500
C5—H50.9500
C8—O1—C1117.19 (19)O1—C8—C9114.4 (2)
C8—N1—C15115.8 (2)N2—C9—C8122.2 (2)
C9—N2—C10116.9 (2)N2—C9—H9118.9
C2—C1—C6120.0C8—C9—H9118.9
C2—C1—O1125.13 (17)N2—C10—C15120.2 (2)
C6—C1—O1114.68 (17)N2—C10—C11120.2 (2)
C1—C2—C3120.0C15—C10—C11119.6 (2)
C1—C2—H2120.0C12—C11—C10121.2 (3)
C3—C2—H2120.0C12—C11—H11119.4
C2—C3—C4120.0C10—C11—H11119.4
C2—C3—H3120.0C11—C12—C13119.4 (3)
C4—C3—H3120.0C11—C12—H12120.3
C5—C4—C3120.0C13—C12—H12120.3
C5—C4—H4120.0C14—C13—C12120.4 (3)
C3—C4—H4120.0C14—C13—H13119.8
C4—C5—C6120.0C12—C13—H13119.8
C4—C5—H5120.0C13—C14—C15121.3 (3)
C6—C5—H5120.0C13—C14—H14119.4
C5—C6—C1120.0C15—C14—H14119.4
C5—C6—C7119.7 (3)N1—C15—C10121.5 (2)
C1—C6—C7120.3 (3)N1—C15—C14120.4 (2)
N1—C8—O1122.3 (2)C10—C15—C14118.1 (3)
N1—C8—C9123.4 (2)
C8—O1—C1—C287.53 (18)C1i—O1—C8—C9160.91 (12)
C1i—O1—C1—C2−173.48 (14)C10—N2—C9—C80.000 (2)
C8—O1—C1—C6−97.56 (16)N1—C8—C9—N20.000 (2)
C1i—O1—C1—C61.43 (19)O1—C8—C9—N2180.000 (1)
C6—C1—C2—C30.0C9—N2—C10—C150.000 (2)
O1—C1—C2—C3174.7 (2)C9—N2—C10—C11180.000 (2)
C1—C2—C3—C40.0N2—C10—C11—C12180.000 (2)
C2—C3—C4—C50.0C15—C10—C11—C120.000 (2)
C3—C4—C5—C60.0C10—C11—C12—C130.000 (2)
C4—C5—C6—C10.0C11—C12—C13—C140.000 (2)
C4—C5—C6—C7−178.3 (4)C12—C13—C14—C150.000 (2)
C2—C1—C6—C50.0C8—N1—C15—C100.000 (1)
O1—C1—C6—C5−175.2 (2)C8—N1—C15—C14180.000 (1)
C2—C1—C6—C7178.2 (4)N2—C10—C15—N10.000 (2)
O1—C1—C6—C73.0 (4)C11—C10—C15—N1180.000 (1)
C15—N1—C8—O1180.000 (1)N2—C10—C15—C14180.000 (2)
C15—N1—C8—C90.000 (1)C11—C10—C15—C140.000 (2)
C1—O1—C8—N119.09 (12)C13—C14—C15—N1180.000 (2)
C1i—O1—C8—N1−19.09 (12)C13—C14—C15—C100.000 (2)
C1—O1—C8—C9−160.91 (12)

Symmetry codes: (i) x, −y+1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2769).

References

  • Abdullah, Z. (2005). Int. J. Chem. Sci.3, 9–15.
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Kawai, M., Lee, M. J., Evans, K. O. & Norlund, T. (2001). J. Fluoresc.11, 23–32.
  • Mohd Salleh, N., Ling, L. P., Abdullah, Z. M. A. A. & Aiyub, Z. (2007). Malays. J. Anal. Sci.11, 229–236.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2008). publCIF In preparation.

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