pmc logo image
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
Your browser version may not work well with NCBI's web applications. More information here...

Formats:

Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1820.
Published online 2008 August 23. doi: 10.1107/S1600536808026809.
PMCID: PMC2960479
Phenyl quinoxalin-2-yl ether
Nor Duha Hassan,a Hairul Anuar Tajuddin,a Zanariah Abdullah,a and Seik Weng Nga*
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng/at/um.edu.my
Received August 18, 2008; Accepted August 19, 2008.
Abstract
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)°.
Related literature
The title compound exhibits fluorescence; see: Abdullah (2005 [triangle]); Kawai et al. (2001 [triangle]); Mohd Salleh et al. (2007 [triangle]). For the only previously reported structural example of a quinoxalin­oxy compound, see: Csikós et al. (1999 [triangle]).
Click on image to enlarge
An external file that holds a picture, illustration, etc.
Object name is e-64-o1820-scheme1.jpg Object name is e-64-o1820-scheme1.jpg
Crystal data
  • C14H10N2O
  • M r = 222.24
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1820-efi1.jpg
  • a = 18.175 (2) Å
  • b = 6.6589 (8) Å
  • c = 19.488 (2) Å
  • β = 112.937 (2)°
  • V = 2172.1 (5) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 (2) K
  • 0.30 × 0.20 × 0.05 mm
Data collection
  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 6018 measured reflections
  • 2478 independent reflections
  • 1909 reflections with I > 2σ(I)
  • R int = 0.026
Refinement
  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.104
  • S = 1.07
  • 2478 reflections
  • 154 parameters
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.27 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/S1600536808026809/tk2297sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026809/tk2297Isup2.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
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).
Experimental
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
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).
Figures
Fig. 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.
Crystal data
C14H10N2OF000 = 928
Mr = 222.24Dx = 1.359 Mg m3
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 mm1
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
Bruker SMART APEX diffractometer1909 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
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 Å3
154 parametersΔρmin = −0.27 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
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)
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, °)
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)
 
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2297).
  • 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.

See more articles cited in this paragraph