Phenyl quinoxalin-2-yl ether

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

doi:10.1107/S1600536808026809

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1820

doi:10.1107/S1600536808026809

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Phenyl quinoxalin-2-yl ether

Nor Duha Hassan,^a Hairul Anuar Tajuddin,^a Zanariah Abdullah ^a and Seik Weng Ng ^a ^*

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

(Received 18 August 2008; accepted 19 August 2008; online 23 August 2008)

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 ); Kawai et al. (2001 ); Mohd Salleh et al. (2007 ). For the only previously reported structural example of a quinoxalinoxy compound, see: Csikós et al. (1999 ).

Experimental

Crystal data

C₁₄H₁₀N₂O
M_r = 222.24
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.104
S = 1.07
2478 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: APEX2 (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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026809/tk2297sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808026809/tk2297Isup2.hkl

checkCIF report

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).

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

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

C₁₄H₁₀N₂O	F(000) = 928
M_r = 222.24	D_x = 1.359 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1614 reflections
a = 18.175 (2) Å	θ = 2.4–28.2°
b = 6.6589 (8) Å	µ = 0.09 mm⁻¹
c = 19.488 (2) Å	T = 100 K
β = 112.937 (2)°	Prism, colorless
V = 2172.1 (5) Å³	0.30 × 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 tube	R_int = 0.026
Graphite monochromator	θ_max = 27.5°, θ_min = 2.3°
ω scans	h = −23→16
6018 measured reflections	k = −8→8
2478 independent reflections	l = −23→25

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0479P)² + 0.7132P] where P = (F_o² + 2F_c²)/3
2478 reflections	(Δ/σ)_max = 0.001
154 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₄H₁₀N₂O	V = 2172.1 (5) Å³
M_r = 222.24	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 18.175 (2) Å	µ = 0.09 mm⁻¹
b = 6.6589 (8) Å	T = 100 K
c = 19.488 (2) Å	0.30 × 0.20 × 0.05 mm
β = 112.937 (2)°

Data collection top

Bruker SMART APEX diffractometer	1909 reflections with I > 2σ(I)
6018 measured reflections	R_int = 0.026
2478 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.07	Δρ_max = 0.27 e Å⁻³
2478 reflections	Δρ_min = −0.27 e Å⁻³
154 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.68658 (5)	0.68613 (14)	0.55215 (5)	0.0196 (2)
N1	0.59181 (6)	0.76551 (15)	0.59977 (6)	0.0166 (2)
N2	0.47638 (6)	0.72591 (16)	0.45219 (6)	0.0176 (2)
C1	0.74734 (7)	0.7128 (2)	0.62327 (7)	0.0178 (3)
C2	0.75301 (8)	0.5866 (2)	0.68141 (8)	0.0242 (3)
H2	0.7143	0.4846	0.6749	0.029*
C3	0.81628 (9)	0.6118 (2)	0.74933 (8)	0.0291 (4)
H3	0.8209	0.5269	0.7900	0.035*
C4	0.87301 (9)	0.7599 (2)	0.75850 (8)	0.0293 (4)
H4	0.9163	0.7763	0.8053	0.035*
C5	0.86637 (8)	0.8838 (2)	0.69930 (8)	0.0267 (3)
H5	0.9053	0.9849	0.7055	0.032*
C6	0.80290 (8)	0.8608 (2)	0.63088 (7)	0.0208 (3)
H6	0.7980	0.9456	0.5901	0.025*
C7	0.60973 (7)	0.71759 (18)	0.54400 (7)	0.0167 (3)
C8	0.55218 (8)	0.69640 (19)	0.46909 (7)	0.0180 (3)
H8	0.5698	0.6599	0.4309	0.022*
C9	0.45400 (7)	0.77709 (18)	0.50983 (7)	0.0156 (3)
C10	0.37309 (8)	0.81243 (19)	0.49536 (7)	0.0184 (3)
H10	0.3341	0.8006	0.4460	0.022*
C11	0.35029 (8)	0.86377 (19)	0.55218 (7)	0.0202 (3)
H11	0.2955	0.8882	0.5420	0.024*
C12	0.40760 (8)	0.8806 (2)	0.62563 (7)	0.0204 (3)
H12	0.3912	0.9162	0.6647	0.025*
C13	0.48681 (8)	0.8460 (2)	0.64120 (7)	0.0189 (3)
H13	0.5249	0.8564	0.6910	0.023*
C14	0.51180 (7)	0.79510 (18)	0.58369 (7)	0.0157 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0157 (5)	0.0261 (5)	0.0182 (5)	0.0021 (4)	0.0079 (4)	−0.0013 (4)
N1	0.0167 (6)	0.0160 (5)	0.0179 (5)	−0.0007 (4)	0.0077 (4)	−0.0009 (4)
N2	0.0214 (6)	0.0154 (5)	0.0166 (5)	−0.0008 (4)	0.0079 (4)	−0.0009 (4)
C1	0.0158 (6)	0.0218 (6)	0.0172 (6)	0.0052 (5)	0.0079 (5)	−0.0004 (5)
C2	0.0238 (7)	0.0257 (7)	0.0295 (7)	0.0071 (6)	0.0174 (6)	0.0064 (6)
C3	0.0297 (8)	0.0404 (9)	0.0233 (7)	0.0181 (7)	0.0169 (6)	0.0118 (6)
C4	0.0222 (7)	0.0439 (9)	0.0184 (7)	0.0127 (7)	0.0045 (6)	−0.0019 (6)
C5	0.0208 (7)	0.0291 (7)	0.0277 (7)	0.0011 (6)	0.0067 (6)	−0.0045 (6)
C6	0.0196 (7)	0.0228 (7)	0.0215 (7)	0.0036 (5)	0.0097 (6)	0.0029 (5)
C7	0.0161 (6)	0.0148 (6)	0.0208 (6)	−0.0003 (5)	0.0090 (5)	0.0005 (5)
C8	0.0221 (7)	0.0164 (6)	0.0176 (6)	−0.0006 (5)	0.0102 (5)	−0.0007 (5)
C9	0.0182 (6)	0.0120 (6)	0.0170 (6)	−0.0008 (5)	0.0074 (5)	−0.0006 (5)
C10	0.0177 (7)	0.0159 (6)	0.0185 (6)	−0.0008 (5)	0.0037 (5)	0.0000 (5)
C11	0.0149 (6)	0.0189 (6)	0.0270 (7)	0.0001 (5)	0.0084 (5)	0.0006 (5)
C12	0.0220 (7)	0.0213 (6)	0.0215 (6)	−0.0001 (5)	0.0123 (6)	−0.0019 (5)
C13	0.0196 (7)	0.0205 (6)	0.0168 (6)	−0.0005 (5)	0.0072 (5)	−0.0009 (5)
C14	0.0152 (6)	0.0133 (6)	0.0184 (6)	−0.0006 (5)	0.0062 (5)	0.0003 (5)

Geometric parameters (Å, º) top

O1—C7	1.3591 (15)	C5—H5	0.9500
O1—C1	1.4068 (15)	C6—H6	0.9500
N1—C7	1.2904 (17)	C7—C8	1.4335 (17)
N1—C14	1.3771 (16)	C8—H8	0.9500
N2—C8	1.3006 (17)	C9—C10	1.4051 (18)
N2—C9	1.3782 (17)	C9—C14	1.4182 (17)
C1—C6	1.3769 (19)	C10—C11	1.3685 (19)
C1—C2	1.3821 (18)	C10—H10	0.9500
C2—C3	1.384 (2)	C11—C12	1.4086 (18)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.387 (2)	C12—C13	1.3703 (18)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.385 (2)	C13—C14	1.4048 (18)
C4—H4	0.9500	C13—H13	0.9500
C5—C6	1.3903 (18)

C7—O1—C1	118.16 (10)	O1—C7—C8	114.37 (11)
C7—N1—C14	115.75 (11)	N2—C8—C7	121.57 (12)
C8—N2—C9	116.80 (11)	N2—C8—H8	119.2
C6—C1—C2	121.99 (12)	C7—C8—H8	119.2
C6—C1—O1	117.24 (11)	N2—C9—C10	119.73 (11)
C2—C1—O1	120.65 (12)	N2—C9—C14	120.73 (12)
C1—C2—C3	118.61 (14)	C10—C9—C14	119.54 (12)
C1—C2—H2	120.7	C11—C10—C9	120.18 (12)
C3—C2—H2	120.7	C11—C10—H10	119.9
C2—C3—C4	120.54 (13)	C9—C10—H10	119.9
C2—C3—H3	119.7	C10—C11—C12	120.33 (12)
C4—C3—H3	119.7	C10—C11—H11	119.8
C5—C4—C3	119.82 (13)	C12—C11—H11	119.8
C5—C4—H4	120.1	C13—C12—C11	120.57 (12)
C3—C4—H4	120.1	C13—C12—H12	119.7
C4—C5—C6	120.25 (14)	C11—C12—H12	119.7
C4—C5—H5	119.9	C12—C13—C14	120.16 (12)
C6—C5—H5	119.9	C12—C13—H13	119.9
C1—C6—C5	118.80 (13)	C14—C13—H13	119.9
C1—C6—H6	120.6	N1—C14—C13	119.60 (11)
C5—C6—H6	120.6	N1—C14—C9	121.18 (12)
N1—C7—O1	121.67 (11)	C13—C14—C9	119.22 (12)
N1—C7—C8	123.96 (12)

C7—O1—C1—C6	−117.62 (13)	O1—C7—C8—N2	−178.58 (11)
C7—O1—C1—C2	66.18 (16)	C8—N2—C9—C10	179.57 (11)
C6—C1—C2—C3	0.5 (2)	C8—N2—C9—C14	−0.26 (17)
O1—C1—C2—C3	176.56 (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—C5	0.0 (2)	C9—C10—C11—C12	−0.3 (2)
C3—C4—C5—C6	0.3 (2)	C10—C11—C12—C13	0.0 (2)
C2—C1—C6—C5	−0.2 (2)	C11—C12—C13—C14	0.6 (2)
O1—C1—C6—C5	−176.37 (11)	C7—N1—C14—C13	179.44 (12)
C4—C5—C6—C1	−0.2 (2)	C7—N1—C14—C9	−1.19 (17)
C14—N1—C7—O1	179.35 (11)	C12—C13—C14—N1	178.41 (11)
C14—N1—C7—C8	0.49 (18)	C12—C13—C14—C9	−0.98 (19)
C1—O1—C7—N1	−1.81 (18)	N2—C9—C14—N1	1.12 (18)
C1—O1—C7—C8	177.15 (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—N2	0.3 (2)	C10—C9—C14—C13	0.68 (18)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀N₂O
M_r	222.24
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	18.175 (2), 6.6589 (8), 19.488 (2)
β (°)	112.937 (2)
V (Å³)	2172.1 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6018, 2478, 1909
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.104, 1.07
No. of reflections	2478
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.27

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

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