Quinoxalin-2-yl p-tolyl ether

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

doi:10.1107/S1600536808026834

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1823

doi:10.1107/S1600536808026834

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Quinoxalin-2-yl p-tolyl 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 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 ); Kawai et al. (2001 ); Mohd Salleh et al. (2007 ).

Experimental

Crystal data

C₁₅H₁₂N₂O
M_r = 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)
R_int = 0.012

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.099
S = 0.99
2030 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.23 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/S1600536808026834/bt2771sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808026834/bt2771Isup2.hkl

checkCIF report

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.

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. 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

C₁₅H₁₂N₂O	Z = 2
M_r = 236.27	F(000) = 248
Triclinic, P1	D_x = 1.331 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.2655 (1) Å	Cell parameters from 2687 reflections
b = 9.1713 (2) Å	θ = 2.3–28.3°
c = 12.8112 (2) Å	µ = 0.09 mm⁻¹
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 tube	R_int = 0.012
Graphite monochromator	θ_max = 25.0°, θ_min = 2.3°
ω scans	h = −6→6
2828 measured reflections	k = −7→10
2030 independent reflections	l = −15→15

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0589P)² + 0.1439P] where P = (F_o² + 2F_c²)/3
2030 reflections	(Δ/σ)_max = 0.001
164 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₅H₁₂N₂O	γ = 89.095 (1)°
M_r = 236.27	V = 589.35 (2) Å³
Triclinic, P1	Z = 2
a = 5.2655 (1) Å	Mo Kα radiation
b = 9.1713 (2) Å	µ = 0.09 mm⁻¹
c = 12.8112 (2) Å	T = 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 reflections	R_int = 0.012
2030 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 0.99	Δρ_max = 0.15 e Å⁻³
2030 reflections	Δρ_min = −0.23 e Å⁻³
164 parameters

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

	x	y	z	U_iso*/U_eq
O1	1.26514 (16)	1.02668 (10)	0.14690 (7)	0.0230 (2)
N1	1.07057 (19)	0.73809 (12)	0.03457 (8)	0.0218 (3)
N2	0.91228 (18)	0.86256 (11)	0.21386 (8)	0.0189 (2)
C1	1.1133 (2)	0.91123 (13)	0.14121 (10)	0.0188 (3)
C2	1.1953 (2)	0.84960 (14)	0.05056 (10)	0.0216 (3)
H2	1.3450	0.8912	0.0006	0.026*
C3	0.8547 (2)	0.68201 (13)	0.10938 (10)	0.0192 (3)
C4	0.7105 (2)	0.56145 (14)	0.09688 (10)	0.0232 (3)
H4	0.7628	0.5188	0.0373	0.028*
C5	0.4948 (2)	0.50557 (14)	0.17061 (11)	0.0245 (3)
H5	0.3980	0.4242	0.1619	0.029*
C6	0.4161 (2)	0.56796 (14)	0.25901 (10)	0.0237 (3)
H6	0.2654	0.5290	0.3093	0.028*
C7	0.5546 (2)	0.68464 (14)	0.27340 (10)	0.0217 (3)
H7	0.5005	0.7252	0.3339	0.026*
C8	0.7766 (2)	0.74447 (13)	0.19880 (10)	0.0181 (3)
C9	1.1976 (2)	1.09150 (13)	0.23540 (10)	0.0199 (3)
C10	0.9936 (2)	1.18709 (14)	0.23647 (10)	0.0232 (3)
H10	0.8934	1.2083	0.1788	0.028*
C11	0.9373 (2)	1.25183 (14)	0.32362 (10)	0.0229 (3)
H11	0.7965	1.3177	0.3252	0.028*
C12	1.0819 (2)	1.22244 (13)	0.40840 (10)	0.0212 (3)
C13	1.2913 (2)	1.12925 (14)	0.40226 (11)	0.0259 (3)
H13	1.3958	1.1102	0.4584	0.031*
C14	1.3511 (2)	1.06353 (14)	0.31607 (11)	0.0241 (3)
H14	1.4953	1.0004	0.3127	0.029*
C15	1.0175 (3)	1.29050 (15)	0.50378 (10)	0.0292 (3)
H15A	0.8638	1.3514	0.4951	0.044*
H15B	1.1620	1.3549	0.5063	0.044*
H15C	0.9849	1.2095	0.5720	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0225 (4)	0.0229 (5)	0.0243 (5)	−0.0055 (4)	0.0043 (4)	−0.0114 (4)
N1	0.0235 (5)	0.0231 (6)	0.0198 (5)	0.0028 (4)	−0.0031 (4)	−0.0081 (4)
N2	0.0203 (5)	0.0176 (5)	0.0190 (5)	0.0008 (4)	−0.0021 (4)	−0.0059 (4)
C1	0.0191 (6)	0.0163 (6)	0.0209 (6)	0.0011 (5)	−0.0032 (5)	−0.0048 (5)
C2	0.0219 (6)	0.0229 (6)	0.0194 (6)	0.0010 (5)	−0.0007 (5)	−0.0058 (5)
C3	0.0204 (6)	0.0189 (6)	0.0191 (6)	0.0046 (5)	−0.0051 (5)	−0.0054 (5)
C4	0.0275 (7)	0.0217 (7)	0.0246 (7)	0.0050 (5)	−0.0084 (5)	−0.0114 (5)
C5	0.0258 (7)	0.0187 (6)	0.0311 (7)	−0.0003 (5)	−0.0093 (5)	−0.0075 (5)
C6	0.0219 (6)	0.0200 (6)	0.0270 (7)	−0.0009 (5)	−0.0021 (5)	−0.0030 (5)
C7	0.0227 (6)	0.0202 (6)	0.0221 (6)	0.0022 (5)	−0.0016 (5)	−0.0064 (5)
C8	0.0202 (6)	0.0155 (6)	0.0193 (6)	0.0033 (5)	−0.0053 (5)	−0.0046 (5)
C9	0.0211 (6)	0.0180 (6)	0.0202 (6)	−0.0061 (5)	0.0031 (5)	−0.0073 (5)
C10	0.0219 (6)	0.0259 (7)	0.0234 (7)	0.0000 (5)	−0.0051 (5)	−0.0081 (5)
C11	0.0194 (6)	0.0233 (7)	0.0273 (7)	0.0020 (5)	−0.0015 (5)	−0.0099 (5)
C12	0.0266 (6)	0.0158 (6)	0.0197 (6)	−0.0059 (5)	−0.0002 (5)	−0.0037 (5)
C13	0.0314 (7)	0.0206 (7)	0.0278 (7)	0.0010 (5)	−0.0120 (6)	−0.0062 (5)
C14	0.0228 (6)	0.0174 (6)	0.0336 (7)	0.0013 (5)	−0.0060 (5)	−0.0088 (5)
C15	0.0395 (8)	0.0260 (7)	0.0221 (7)	−0.0036 (6)	−0.0014 (6)	−0.0083 (6)

Geometric parameters (Å, º) top

O1—C1	1.3606 (14)	C7—C8	1.4072 (17)
O1—C9	1.4112 (14)	C7—H7	0.9500
N1—C2	1.3010 (16)	C9—C10	1.3765 (18)
N1—C3	1.3776 (16)	C9—C14	1.3774 (18)
N2—C1	1.2954 (15)	C10—C11	1.3894 (17)
N2—C8	1.3777 (15)	C10—H10	0.9500
C1—C2	1.4285 (17)	C11—C12	1.3877 (18)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.4080 (17)	C12—C13	1.3898 (18)
C3—C8	1.4159 (17)	C12—C15	1.5057 (17)
C4—C5	1.3701 (18)	C13—C14	1.3860 (18)
C4—H4	0.9500	C13—H13	0.9500
C5—C6	1.4046 (18)	C14—H14	0.9500
C5—H5	0.9500	C15—H15A	0.9800
C6—C7	1.3717 (17)	C15—H15B	0.9800
C6—H6	0.9500	C15—H15C	0.9800

C1—O1—C9	117.73 (9)	C7—C8—C3	119.03 (11)
C2—N1—C3	116.77 (10)	C10—C9—C14	121.60 (12)
C1—N2—C8	115.51 (10)	C10—C9—O1	120.33 (11)
N2—C1—O1	121.46 (10)	C14—C9—O1	117.94 (11)
N2—C1—C2	123.85 (11)	C9—C10—C11	118.64 (11)
O1—C1—C2	114.69 (10)	C9—C10—H10	120.7
N1—C2—C1	121.82 (11)	C11—C10—H10	120.7
N1—C2—H2	119.1	C12—C11—C10	121.49 (11)
C1—C2—H2	119.1	C12—C11—H11	119.3
N1—C3—C4	119.73 (11)	C10—C11—H11	119.3
N1—C3—C8	120.60 (11)	C11—C12—C13	117.97 (11)
C4—C3—C8	119.67 (11)	C11—C12—C15	121.39 (11)
C5—C4—C3	120.09 (12)	C13—C12—C15	120.63 (11)
C5—C4—H4	120.0	C14—C13—C12	121.48 (12)
C3—C4—H4	120.0	C14—C13—H13	119.3
C4—C5—C6	120.34 (11)	C12—C13—H13	119.3
C4—C5—H5	119.8	C9—C14—C13	118.74 (11)
C6—C5—H5	119.8	C9—C14—H14	120.6
C7—C6—C5	120.65 (11)	C13—C14—H14	120.6
C7—C6—H6	119.7	C12—C15—H15A	109.5
C5—C6—H6	119.7	C12—C15—H15B	109.5
C6—C7—C8	120.23 (11)	H15A—C15—H15B	109.5
C6—C7—H7	119.9	C12—C15—H15C	109.5
C8—C7—H7	119.9	H15A—C15—H15C	109.5
N2—C8—C7	119.52 (11)	H15B—C15—H15C	109.5
N2—C8—C3	121.45 (11)

C8—N2—C1—O1	−179.56 (9)	C6—C7—C8—C3	−0.28 (17)
C8—N2—C1—C2	−0.09 (17)	N1—C3—C8—N2	0.09 (17)
C9—O1—C1—N2	0.45 (16)	C4—C3—C8—N2	−179.94 (10)
C9—O1—C1—C2	−179.07 (10)	N1—C3—C8—C7	179.79 (10)
C3—N1—C2—C1	0.04 (17)	C4—C3—C8—C7	−0.23 (17)
N2—C1—C2—N1	0.07 (19)	C1—O1—C9—C10	−75.16 (14)
O1—C1—C2—N1	179.57 (10)	C1—O1—C9—C14	108.80 (12)
C2—N1—C3—C4	179.91 (10)	C14—C9—C10—C11	−2.43 (18)
C2—N1—C3—C8	−0.11 (16)	O1—C9—C10—C11	−178.32 (10)
N1—C3—C4—C5	−179.65 (10)	C9—C10—C11—C12	0.18 (18)
C8—C3—C4—C5	0.37 (18)	C10—C11—C12—C13	1.90 (18)
C3—C4—C5—C6	0.00 (18)	C10—C11—C12—C15	−178.87 (11)
C4—C5—C6—C7	−0.53 (19)	C11—C12—C13—C14	−1.86 (18)
C5—C6—C7—C8	0.67 (18)	C15—C12—C13—C14	178.91 (11)
C1—N2—C8—C7	−179.68 (10)	C10—C9—C14—C13	2.47 (18)
C1—N2—C8—C3	0.02 (16)	O1—C9—C14—C13	178.45 (10)
C6—C7—C8—N2	179.42 (10)	C12—C13—C14—C9	−0.27 (18)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂N₂O
M_r	236.27
Crystal system, space group	Triclinic, 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)
V (Å³)	589.35 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.25 × 0.25

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2828, 2030, 1764
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.099, 0.99
No. of reflections	2030
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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

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