supplementary materials


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

tk2297 scheme

Acta Cryst. (2008). E64, o1820    [ doi:10.1107/S1600536808026809 ]

Phenyl quinoxalin-2-yl ether

N. D. Hassan, H. A. Tajuddin, Z. Abdullah and S. W. Ng

Abstract top

The aromatic ring systems in the title compound, C14H10N2O, form a dihedral angle of 63.8 (1)°, resulting in an opening up of the ether-O atom angle to 118.2 (1)°.

Comment top

The title compound (I) belongs to a class of compounds that exhibits fluorescence (Abdullah, 2005; Kawai et al., 2001; Mohd Salleh et al., 2007). In the crystal structure, the two aromatic systems aligned at 63.8 (1) °; these open up the angle at the oxygen atom to 118.2 (1) ° (Fig. 1).

In the structural literature, there is only one example of a quinoxalinoxy compound, 2(1H-quinoxalone O-(2'-quinoxalinyl)hydroxylamine, which exists in two colored forms (Csikós et al., 1999).

Related literature top

The title compound exhibits fluorescence; see: Abdullah (2005); Kawai et al. (2001); Mohd Salleh et al. (2007). For the only structural example of a quinoxalinoxy compound, see: Csikós et al. (1999).

Experimental top

Phenol (0.47 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 of (I).

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 Å) and were included in the refinement in the riding model approximation, with U(H) fixed at 1.2U(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 (I) drawn at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Phenyl quinoxalin-2-yl ether top
Crystal data top
C14H10N2OF000 = 928
Mr = 222.24Dx = 1.359 Mg m−3
Monoclinic, C2/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1614 reflections
a = 18.175 (2) Åθ = 2.4–28.2º
b = 6.6589 (8) ŵ = 0.09 mm−1
c = 19.488 (2) ÅT = 100 (2) K
β = 112.937 (2)ºPrism, colorless
V = 2172.1 (5) Å30.30 × 0.20 × 0.05 mm
Z = 8
Data collection top
Bruker SMART APEX
diffractometer		1909 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Monochromator: graphiteθmax = 27.5º
T = 100(2) Kθmin = 2.3º
ω scansh = −23→16
Absorption correction: Nonek = −8→8
6018 measured reflectionsl = −23→25
2478 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.104  w = 1/[σ2(Fo2) + (0.0479P)2 + 0.7132P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
2478 reflectionsΔρmax = 0.27 e Å−3
154 parametersΔρmin = −0.27 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C14H10N2OV = 2172.1 (5) Å3
Mr = 222.24Z = 8
Monoclinic, C2/cMo Kα
a = 18.175 (2) ŵ = 0.09 mm−1
b = 6.6589 (8) ÅT = 100 (2) K
c = 19.488 (2) Å0.30 × 0.20 × 0.05 mm
β = 112.937 (2)º
Data collection top
Bruker SMART APEX
diffractometer		2478 independent reflections
Absorption correction: None1909 reflections with I > 2σ(I)
6018 measured reflectionsRint = 0.026
Refinement top
R[F2 > 2σ(F2)] = 0.039154 parameters
wR(F2) = 0.104H-atom parameters constrained
S = 1.07Δρmax = 0.27 e Å−3
2478 reflectionsΔρmin = −0.27 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.68658 (5)0.68613 (14)0.55215 (5)0.0196 (2)
N10.59181 (6)0.76551 (15)0.59977 (6)0.0166 (2)
N20.47638 (6)0.72591 (16)0.45219 (6)0.0176 (2)
C10.74734 (7)0.7128 (2)0.62327 (7)0.0178 (3)
C20.75301 (8)0.5866 (2)0.68141 (8)0.0242 (3)
H20.71430.48460.67490.029*
C30.81628 (9)0.6118 (2)0.74933 (8)0.0291 (4)
H30.82090.52690.79000.035*
C40.87301 (9)0.7599 (2)0.75850 (8)0.0293 (4)
H40.91630.77630.80530.035*
C50.86637 (8)0.8838 (2)0.69930 (8)0.0267 (3)
H50.90530.98490.70550.032*
C60.80290 (8)0.8608 (2)0.63088 (7)0.0208 (3)
H60.79800.94560.59010.025*
C70.60973 (7)0.71759 (18)0.54400 (7)0.0167 (3)
C80.55218 (8)0.69640 (19)0.46909 (7)0.0180 (3)
H80.56980.65990.43090.022*
C90.45400 (7)0.77709 (18)0.50983 (7)0.0156 (3)
C100.37309 (8)0.81243 (19)0.49536 (7)0.0184 (3)
H100.33410.80060.44600.022*
C110.35029 (8)0.86377 (19)0.55218 (7)0.0202 (3)
H110.29550.88820.54200.024*
C120.40760 (8)0.8806 (2)0.62563 (7)0.0204 (3)
H120.39120.91620.66470.025*
C130.48681 (8)0.8460 (2)0.64120 (7)0.0189 (3)
H130.52490.85640.69100.023*
C140.51180 (7)0.79510 (18)0.58369 (7)0.0157 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0157 (5)0.0261 (5)0.0182 (5)0.0021 (4)0.0079 (4)−0.0013 (4)
N10.0167 (6)0.0160 (5)0.0179 (5)−0.0007 (4)0.0077 (4)−0.0009 (4)
N20.0214 (6)0.0154 (5)0.0166 (5)−0.0008 (4)0.0079 (4)−0.0009 (4)
C10.0158 (6)0.0218 (6)0.0172 (6)0.0052 (5)0.0079 (5)−0.0004 (5)
C20.0238 (7)0.0257 (7)0.0295 (7)0.0071 (6)0.0174 (6)0.0064 (6)
C30.0297 (8)0.0404 (9)0.0233 (7)0.0181 (7)0.0169 (6)0.0118 (6)
C40.0222 (7)0.0439 (9)0.0184 (7)0.0127 (7)0.0045 (6)−0.0019 (6)
C50.0208 (7)0.0291 (7)0.0277 (7)0.0011 (6)0.0067 (6)−0.0045 (6)
C60.0196 (7)0.0228 (7)0.0215 (7)0.0036 (5)0.0097 (6)0.0029 (5)
C70.0161 (6)0.0148 (6)0.0208 (6)−0.0003 (5)0.0090 (5)0.0005 (5)
C80.0221 (7)0.0164 (6)0.0176 (6)−0.0006 (5)0.0102 (5)−0.0007 (5)
C90.0182 (6)0.0120 (6)0.0170 (6)−0.0008 (5)0.0074 (5)−0.0006 (5)
C100.0177 (7)0.0159 (6)0.0185 (6)−0.0008 (5)0.0037 (5)0.0000 (5)
C110.0149 (6)0.0189 (6)0.0270 (7)0.0001 (5)0.0084 (5)0.0006 (5)
C120.0220 (7)0.0213 (6)0.0215 (6)−0.0001 (5)0.0123 (6)−0.0019 (5)
C130.0196 (7)0.0205 (6)0.0168 (6)−0.0005 (5)0.0072 (5)−0.0009 (5)
C140.0152 (6)0.0133 (6)0.0184 (6)−0.0006 (5)0.0062 (5)0.0003 (5)
Geometric parameters (Å, °) top
O1—C71.3591 (15)C5—H50.9500
O1—C11.4068 (15)C6—H60.9500
N1—C71.2904 (17)C7—C81.4335 (17)
N1—C141.3771 (16)C8—H80.9500
N2—C81.3006 (17)C9—C101.4051 (18)
N2—C91.3782 (17)C9—C141.4182 (17)
C1—C61.3769 (19)C10—C111.3685 (19)
C1—C21.3821 (18)C10—H100.9500
C2—C31.384 (2)C11—C121.4086 (18)
C2—H20.9500C11—H110.9500
C3—C41.387 (2)C12—C131.3703 (18)
C3—H30.9500C12—H120.9500
C4—C51.385 (2)C13—C141.4048 (18)
C4—H40.9500C13—H130.9500
C5—C61.3903 (18)
C7—O1—C1118.16 (10)O1—C7—C8114.37 (11)
C7—N1—C14115.75 (11)N2—C8—C7121.57 (12)
C8—N2—C9116.80 (11)N2—C8—H8119.2
C6—C1—C2121.99 (12)C7—C8—H8119.2
C6—C1—O1117.24 (11)N2—C9—C10119.73 (11)
C2—C1—O1120.65 (12)N2—C9—C14120.73 (12)
C1—C2—C3118.61 (14)C10—C9—C14119.54 (12)
C1—C2—H2120.7C11—C10—C9120.18 (12)
C3—C2—H2120.7C11—C10—H10119.9
C2—C3—C4120.54 (13)C9—C10—H10119.9
C2—C3—H3119.7C10—C11—C12120.33 (12)
C4—C3—H3119.7C10—C11—H11119.8
C5—C4—C3119.82 (13)C12—C11—H11119.8
C5—C4—H4120.1C13—C12—C11120.57 (12)
C3—C4—H4120.1C13—C12—H12119.7
C4—C5—C6120.25 (14)C11—C12—H12119.7
C4—C5—H5119.9C12—C13—C14120.16 (12)
C6—C5—H5119.9C12—C13—H13119.9
C1—C6—C5118.80 (13)C14—C13—H13119.9
C1—C6—H6120.6N1—C14—C13119.60 (11)
C5—C6—H6120.6N1—C14—C9121.18 (12)
N1—C7—O1121.67 (11)C13—C14—C9119.22 (12)
N1—C7—C8123.96 (12)
C7—O1—C1—C6−117.62 (13)O1—C7—C8—N2−178.58 (11)
C7—O1—C1—C266.18 (16)C8—N2—C9—C10179.57 (11)
C6—C1—C2—C30.5 (2)C8—N2—C9—C14−0.26 (17)
O1—C1—C2—C3176.56 (12)N2—C9—C10—C11−179.85 (12)
C1—C2—C3—C4−0.4 (2)C14—C9—C10—C11−0.03 (19)
C2—C3—C4—C50.0 (2)C9—C10—C11—C12−0.3 (2)
C3—C4—C5—C60.3 (2)C10—C11—C12—C130.0 (2)
C2—C1—C6—C5−0.2 (2)C11—C12—C13—C140.6 (2)
O1—C1—C6—C5−176.37 (11)C7—N1—C14—C13179.44 (12)
C4—C5—C6—C1−0.2 (2)C7—N1—C14—C9−1.19 (17)
C14—N1—C7—O1179.35 (11)C12—C13—C14—N1178.41 (11)
C14—N1—C7—C80.49 (18)C12—C13—C14—C9−0.98 (19)
C1—O1—C7—N1−1.81 (18)N2—C9—C14—N11.12 (18)
C1—O1—C7—C8177.15 (10)C10—C9—C14—N1−178.70 (11)
C9—N2—C8—C7−0.45 (18)N2—C9—C14—C13−179.50 (12)
N1—C7—C8—N20.3 (2)C10—C9—C14—C130.68 (18)
Acknowledgements top

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

references
References top

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.

Csikós, É., Ferenczy, G. G., Ángyán, J. G., Böcskei, Z., Simon, K., Gönczi, C., Hermecz, I. & Hermecz, I. (1999). Eur. J. Org. Chem. pp. 2119–2125.

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.

Westrip, S. P. (2008). publCIF. In preparation.