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Quinoxalin-2-yl p-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 42.6 (1)°. The angle at the O atom is widened to 117.7 (1)°.

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

  • Triclinic, [P \overline 1]

  • a = 5.2655 (1) Å

  • b = 9.1713 (2) Å

  • c = 12.8112 (2) Å

  • α = 74.660 (1)°

  • β = 81.163 (1)°

  • γ = 89.095 (1)°

  • V = 589.35 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 100 (2) K

  • 0.25 × 0.25 × 0.25 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: none

  • 2828 measured reflections

  • 2030 independent reflections

  • 1764 reflections with I > 2σ(I)

  • Rint = 0.012

Refinement
  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.099

  • S = 0.99

  • 2030 reflections

  • 164 parameters

  • H-atom parameters constrained

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.23 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 title compound exhibits fluorescence; see: Abdullah (2005); Kawai et al. (2001); Mohd Salleh et al. (2007).

Experimental top

p-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

Carbon-bound 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. Displacement ellipsoid plot (Barbour, 2001) plot of C15H12N2O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
Quinoxalin-2-yl p-tolyl ether top
Crystal data top
C15H12N2OZ = 2
Mr = 236.27F(000) = 248
Triclinic, P1Dx = 1.331 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.2655 (1) ÅCell parameters from 2687 reflections
b = 9.1713 (2) Åθ = 2.3–28.3°
c = 12.8112 (2) ŵ = 0.09 mm1
α = 74.660 (1)°T = 100 K
β = 81.163 (1)°Irregular block, colorless
γ = 89.095 (1)°0.25 × 0.25 × 0.25 mm
V = 589.35 (2) Å3
Data collection top
Bruker SMART APEX
diffractometer
1764 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.012
Graphite monochromatorθmax = 25.0°, θmin = 2.3°
ω scansh = 66
2828 measured reflectionsk = 710
2030 independent reflectionsl = 1515
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0589P)2 + 0.1439P]
where P = (Fo2 + 2Fc2)/3
2030 reflections(Δ/σ)max = 0.001
164 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C15H12N2Oγ = 89.095 (1)°
Mr = 236.27V = 589.35 (2) Å3
Triclinic, P1Z = 2
a = 5.2655 (1) ÅMo Kα radiation
b = 9.1713 (2) ŵ = 0.09 mm1
c = 12.8112 (2) ÅT = 100 K
α = 74.660 (1)°0.25 × 0.25 × 0.25 mm
β = 81.163 (1)°
Data collection top
Bruker SMART APEX
diffractometer
1764 reflections with I > 2σ(I)
2828 measured reflectionsRint = 0.012
2030 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.099H-atom parameters constrained
S = 0.99Δρmax = 0.15 e Å3
2030 reflectionsΔρmin = 0.23 e Å3
164 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O11.26514 (16)1.02668 (10)0.14690 (7)0.0230 (2)
N11.07057 (19)0.73809 (12)0.03457 (8)0.0218 (3)
N20.91228 (18)0.86256 (11)0.21386 (8)0.0189 (2)
C11.1133 (2)0.91123 (13)0.14121 (10)0.0188 (3)
C21.1953 (2)0.84960 (14)0.05056 (10)0.0216 (3)
H21.34500.89120.00060.026*
C30.8547 (2)0.68201 (13)0.10938 (10)0.0192 (3)
C40.7105 (2)0.56145 (14)0.09688 (10)0.0232 (3)
H40.76280.51880.03730.028*
C50.4948 (2)0.50557 (14)0.17061 (11)0.0245 (3)
H50.39800.42420.16190.029*
C60.4161 (2)0.56796 (14)0.25901 (10)0.0237 (3)
H60.26540.52900.30930.028*
C70.5546 (2)0.68464 (14)0.27340 (10)0.0217 (3)
H70.50050.72520.33390.026*
C80.7766 (2)0.74447 (13)0.19880 (10)0.0181 (3)
C91.1976 (2)1.09150 (13)0.23540 (10)0.0199 (3)
C100.9936 (2)1.18709 (14)0.23647 (10)0.0232 (3)
H100.89341.20830.17880.028*
C110.9373 (2)1.25183 (14)0.32362 (10)0.0229 (3)
H110.79651.31770.32520.028*
C121.0819 (2)1.22244 (13)0.40840 (10)0.0212 (3)
C131.2913 (2)1.12925 (14)0.40226 (11)0.0259 (3)
H131.39581.11020.45840.031*
C141.3511 (2)1.06353 (14)0.31607 (11)0.0241 (3)
H141.49531.00040.31270.029*
C151.0175 (3)1.29050 (15)0.50378 (10)0.0292 (3)
H15A0.86381.35140.49510.044*
H15B1.16201.35490.50630.044*
H15C0.98491.20950.57200.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0225 (4)0.0229 (5)0.0243 (5)0.0055 (4)0.0043 (4)0.0114 (4)
N10.0235 (5)0.0231 (6)0.0198 (5)0.0028 (4)0.0031 (4)0.0081 (4)
N20.0203 (5)0.0176 (5)0.0190 (5)0.0008 (4)0.0021 (4)0.0059 (4)
C10.0191 (6)0.0163 (6)0.0209 (6)0.0011 (5)0.0032 (5)0.0048 (5)
C20.0219 (6)0.0229 (6)0.0194 (6)0.0010 (5)0.0007 (5)0.0058 (5)
C30.0204 (6)0.0189 (6)0.0191 (6)0.0046 (5)0.0051 (5)0.0054 (5)
C40.0275 (7)0.0217 (7)0.0246 (7)0.0050 (5)0.0084 (5)0.0114 (5)
C50.0258 (7)0.0187 (6)0.0311 (7)0.0003 (5)0.0093 (5)0.0075 (5)
C60.0219 (6)0.0200 (6)0.0270 (7)0.0009 (5)0.0021 (5)0.0030 (5)
C70.0227 (6)0.0202 (6)0.0221 (6)0.0022 (5)0.0016 (5)0.0064 (5)
C80.0202 (6)0.0155 (6)0.0193 (6)0.0033 (5)0.0053 (5)0.0046 (5)
C90.0211 (6)0.0180 (6)0.0202 (6)0.0061 (5)0.0031 (5)0.0073 (5)
C100.0219 (6)0.0259 (7)0.0234 (7)0.0000 (5)0.0051 (5)0.0081 (5)
C110.0194 (6)0.0233 (7)0.0273 (7)0.0020 (5)0.0015 (5)0.0099 (5)
C120.0266 (6)0.0158 (6)0.0197 (6)0.0059 (5)0.0002 (5)0.0037 (5)
C130.0314 (7)0.0206 (7)0.0278 (7)0.0010 (5)0.0120 (6)0.0062 (5)
C140.0228 (6)0.0174 (6)0.0336 (7)0.0013 (5)0.0060 (5)0.0088 (5)
C150.0395 (8)0.0260 (7)0.0221 (7)0.0036 (6)0.0014 (6)0.0083 (6)
Geometric parameters (Å, º) top
O1—C11.3606 (14)C7—C81.4072 (17)
O1—C91.4112 (14)C7—H70.9500
N1—C21.3010 (16)C9—C101.3765 (18)
N1—C31.3776 (16)C9—C141.3774 (18)
N2—C11.2954 (15)C10—C111.3894 (17)
N2—C81.3777 (15)C10—H100.9500
C1—C21.4285 (17)C11—C121.3877 (18)
C2—H20.9500C11—H110.9500
C3—C41.4080 (17)C12—C131.3898 (18)
C3—C81.4159 (17)C12—C151.5057 (17)
C4—C51.3701 (18)C13—C141.3860 (18)
C4—H40.9500C13—H130.9500
C5—C61.4046 (18)C14—H140.9500
C5—H50.9500C15—H15A0.9800
C6—C71.3717 (17)C15—H15B0.9800
C6—H60.9500C15—H15C0.9800
C1—O1—C9117.73 (9)C7—C8—C3119.03 (11)
C2—N1—C3116.77 (10)C10—C9—C14121.60 (12)
C1—N2—C8115.51 (10)C10—C9—O1120.33 (11)
N2—C1—O1121.46 (10)C14—C9—O1117.94 (11)
N2—C1—C2123.85 (11)C9—C10—C11118.64 (11)
O1—C1—C2114.69 (10)C9—C10—H10120.7
N1—C2—C1121.82 (11)C11—C10—H10120.7
N1—C2—H2119.1C12—C11—C10121.49 (11)
C1—C2—H2119.1C12—C11—H11119.3
N1—C3—C4119.73 (11)C10—C11—H11119.3
N1—C3—C8120.60 (11)C11—C12—C13117.97 (11)
C4—C3—C8119.67 (11)C11—C12—C15121.39 (11)
C5—C4—C3120.09 (12)C13—C12—C15120.63 (11)
C5—C4—H4120.0C14—C13—C12121.48 (12)
C3—C4—H4120.0C14—C13—H13119.3
C4—C5—C6120.34 (11)C12—C13—H13119.3
C4—C5—H5119.8C9—C14—C13118.74 (11)
C6—C5—H5119.8C9—C14—H14120.6
C7—C6—C5120.65 (11)C13—C14—H14120.6
C7—C6—H6119.7C12—C15—H15A109.5
C5—C6—H6119.7C12—C15—H15B109.5
C6—C7—C8120.23 (11)H15A—C15—H15B109.5
C6—C7—H7119.9C12—C15—H15C109.5
C8—C7—H7119.9H15A—C15—H15C109.5
N2—C8—C7119.52 (11)H15B—C15—H15C109.5
N2—C8—C3121.45 (11)
C8—N2—C1—O1179.56 (9)C6—C7—C8—C30.28 (17)
C8—N2—C1—C20.09 (17)N1—C3—C8—N20.09 (17)
C9—O1—C1—N20.45 (16)C4—C3—C8—N2179.94 (10)
C9—O1—C1—C2179.07 (10)N1—C3—C8—C7179.79 (10)
C3—N1—C2—C10.04 (17)C4—C3—C8—C70.23 (17)
N2—C1—C2—N10.07 (19)C1—O1—C9—C1075.16 (14)
O1—C1—C2—N1179.57 (10)C1—O1—C9—C14108.80 (12)
C2—N1—C3—C4179.91 (10)C14—C9—C10—C112.43 (18)
C2—N1—C3—C80.11 (16)O1—C9—C10—C11178.32 (10)
N1—C3—C4—C5179.65 (10)C9—C10—C11—C120.18 (18)
C8—C3—C4—C50.37 (18)C10—C11—C12—C131.90 (18)
C3—C4—C5—C60.00 (18)C10—C11—C12—C15178.87 (11)
C4—C5—C6—C70.53 (19)C11—C12—C13—C141.86 (18)
C5—C6—C7—C80.67 (18)C15—C12—C13—C14178.91 (11)
C1—N2—C8—C7179.68 (10)C10—C9—C14—C132.47 (18)
C1—N2—C8—C30.02 (16)O1—C9—C14—C13178.45 (10)
C6—C7—C8—N2179.42 (10)C12—C13—C14—C90.27 (18)

Experimental details

Crystal data
Chemical formulaC15H12N2O
Mr236.27
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)5.2655 (1), 9.1713 (2), 12.8112 (2)
α, β, γ (°)74.660 (1), 81.163 (1), 89.095 (1)
V3)589.35 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.25 × 0.25 × 0.25
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
2828, 2030, 1764
Rint0.012
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.099, 0.99
No. of reflections2030
No. of parameters164
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.15, 0.23

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. 358/2008 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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