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ISSN: 2056-9890

Quinoxalin-2-yl o-tolyl ether

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 12 August 2008; accepted 19 August 2008; online 23 August 2008)

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[Abdullah, Z. (2005). Int. J. Chem. Sci. 3, 9-15.]); Kawai et al. (2001[Kawai, M., Lee, M. J., Evans, K. O. & Norlund, T. (2001). J. Fluoresc. 11, 23-32.]); Mohd Salleh et al. (2007[Mohd Salleh, N., Ling, L. P., Abdullah, Z. M. A. A. & Aiyub, Z. (2007). Malays. J. Anal. Sci. 11, 229-236.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12N2O

  • Mr = 236.27

  • Monoclinic, P 21 /m

  • 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)

  • Rint = 0.026

Refinement
  • R[F2 > 2σ(F2)] = 0.065

  • wR(F2) = 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[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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, 2008[Westrip, S. P. (2008). publCIF. In preparation.]).

Supporting information


Related literature top

The titlecompound exhibits fluorescence; see: Abdullah (2005); Kawai et al. (2001); Mohd Salleh et al. (2007).

Experimental top

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 top

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).

Computing details top

Data collection: APEX2 software (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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, 2008).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C15H12N2O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Quinoxalin-2-yl o-tolyl ether top
Crystal data top
C15H12N2OF(000) = 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 = 2.7–24.6°
b = 7.413 (1) ŵ = 0.09 mm1
c = 10.596 (2) ÅT = 100 K
β = 108.332 (3)°Block, colorless
V = 587.1 (2) Å30.20 × 0.20 × 0.08 mm
Z = 2
Data collection top
Bruker SMART APEX
diffractometer
1032 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
Graphite monochromatorθmax = 27.5°, θmin = 2.0°
ω scansh = 108
3392 measured reflectionsk = 98
1443 independent reflectionsl = 1213
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.183H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0776P)2 + 0.4106P]
where P = (Fo2 + 2Fc2)/3
1443 reflections(Δ/σ)max = 0.001
119 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
C15H12N2OV = 587.1 (2) Å3
Mr = 236.27Z = 2
Monoclinic, P21/mMo Kα radiation
a = 7.874 (2) ŵ = 0.09 mm1
b = 7.413 (1) ÅT = 100 K
c = 10.596 (2) Å0.20 × 0.20 × 0.08 mm
β = 108.332 (3)°
Data collection top
Bruker SMART APEX
diffractometer
1032 reflections with I > 2σ(I)
3392 measured reflectionsRint = 0.027
1443 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0650 restraints
wR(F2) = 0.183H-atom parameters constrained
S = 1.03Δρmax = 0.24 e Å3
1443 reflectionsΔρmin = 0.31 e Å3
119 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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
H20.20020.07870.54450.056*0.50
C30.2619 (5)0.0199 (3)0.3761 (3)0.0473 (11)0.50
H30.26120.14100.34660.057*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) top
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, º) top
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—C2173.48 (14)C10—N2—C9—C80.000 (2)
C8—O1—C1—C697.56 (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—C7178.3 (4)C12—C13—C14—C150.000 (2)
C2—C1—C6—C50.0C8—N1—C15—C100.000 (1)
O1—C1—C6—C5175.2 (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—N119.09 (12)C13—C14—C15—C100.000 (2)
C1—O1—C8—C9160.91 (12)
Symmetry code: (i) x, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC15H12N2O
Mr236.27
Crystal system, space groupMonoclinic, P21/m
Temperature (K)100
a, b, c (Å)7.874 (2), 7.413 (1), 10.596 (2)
β (°) 108.332 (3)
V3)587.1 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.20 × 0.20 × 0.08
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3392, 1443, 1032
Rint0.027
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.183, 1.03
No. of reflections1443
No. of parameters119
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.31

Computer programs: APEX2 software (Bruker, 2007), SAINT (Bruker, 2007), SAINT, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

 

Acknowledgements

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

References

First citationAbdullah, Z. (2005). Int. J. Chem. Sci. 3, 9–15.  CAS Google Scholar
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationKawai, M., Lee, M. J., Evans, K. O. & Norlund, T. (2001). J. Fluoresc. 11, 23–32.  Web of Science CrossRef CAS Google Scholar
First citationMohd Salleh, N., Ling, L. P., Abdullah, Z. M. A. A. & Aiyub, Z. (2007). Malays. J. Anal. Sci. 11, 229–236.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2008). publCIF. In preparation.  Google Scholar

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