Quinoxalin-2-yl o-tolyl ether

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

doi:10.1107/S1600536808026810

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1821

doi:10.1107/S1600536808026810

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Quinoxalin-2-yl o-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 85.9 (1)°; The angle at the O atom is widened to 118.2 (2)°. The quinoxalinyloxy part of the molecule lies on a mirror plane and the tolyl group is disordered over two positions about the mirror plane.

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
Monoclinic, P 2₁ /m
a = 7.874 (2) Å
b = 7.413 (1) Å
c = 10.596 (2) Å
β = 108.332 (3)°
V = 587.1 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 (2) K
0.20 × 0.20 × 0.08 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
3392 measured reflections
1443 independent reflections
1032 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.183
S = 1.03
1443 reflections
119 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.31 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/S1600536808026810/bt2769sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808026810/bt2769Isup2.hkl

checkCIF report

Related literature top

The titlecompound exhibits fluorescence; see: Abdullah (2005); Kawai et al. (2001); Mohd Salleh et al. (2007).

Experimental top

o-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. Thermal ellipsoid plot (Barbour, 2001) of C₁₅H₁₂N₂O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Quinoxalin-2-yl o-tolyl ether top

Crystal data top

C₁₅H₁₂N₂O	F(000) = 248
M_r = 236.27	D_x = 1.337 Mg m⁻³
Monoclinic, P2₁/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 756 reflections
a = 7.874 (2) Å	θ = 2.7–24.6°
b = 7.413 (1) Å	µ = 0.09 mm⁻¹
c = 10.596 (2) Å	T = 100 K
β = 108.332 (3)°	Block, colorless
V = 587.1 (2) Å³	0.20 × 0.20 × 0.08 mm
Z = 2

Data collection top

Bruker SMART APEX diffractometer	1032 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 27.5°, θ_min = 2.0°
ω scans	h = −10→8
3392 measured reflections	k = −9→8
1443 independent reflections	l = −12→13

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.183	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0776P)² + 0.4106P] where P = (F_o² + 2F_c²)/3
1443 reflections	(Δ/σ)_max = 0.001
119 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₅H₁₂N₂O	V = 587.1 (2) Å³
M_r = 236.27	Z = 2
Monoclinic, P2₁/m	Mo Kα radiation
a = 7.874 (2) Å	µ = 0.09 mm⁻¹
b = 7.413 (1) Å	T = 100 K
c = 10.596 (2) Å	0.20 × 0.20 × 0.08 mm
β = 108.332 (3)°

Data collection top

Bruker SMART APEX diffractometer	1032 reflections with I > 2σ(I)
3392 measured reflections	R_int = 0.027
1443 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.183	H-atom parameters constrained
S = 1.03	Δρ_max = 0.24 e Å⁻³
1443 reflections	Δρ_min = −0.31 e Å⁻³
119 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.1778 (2)	0.2500	0.64890 (18)	0.0405 (6)
N1	0.4752 (3)	0.2500	0.7791 (2)	0.0552 (9)
N2	0.3518 (3)	0.2500	0.9997 (2)	0.0479 (8)
C1	0.2266 (3)	0.1943 (3)	0.5368 (2)	0.0256 (8)	0.50
C2	0.2256 (5)	0.0171 (3)	0.4936 (3)	0.047 (2)	0.50
H2	0.2002	−0.0787	0.5445	0.056*	0.50
C3	0.2619 (5)	−0.0199 (3)	0.3761 (3)	0.0473 (11)	0.50
H3	0.2612	−0.1410	0.3466	0.057*	0.50
C4	0.2991 (4)	0.1203 (4)	0.3017 (2)	0.0417 (12)	0.50
H4	0.3239	0.0950	0.2213	0.050*	0.50
C5	0.3000 (3)	0.2975 (3)	0.3449 (2)	0.0345 (15)	0.50
H5	0.3255	0.3933	0.2940	0.041*	0.50
C6	0.2638 (3)	0.3345 (3)	0.4624 (3)	0.0313 (8)	0.50
C7	0.2599 (11)	0.5228 (12)	0.5056 (7)	0.0496 (17)	0.50
H7A	0.3449	0.5946	0.4761	0.074*	0.50
H7B	0.2932	0.5272	0.6028	0.074*	0.50
H7C	0.1391	0.5719	0.4666	0.074*	0.50
C8	0.3083 (3)	0.2500	0.7686 (2)	0.0300 (6)
C9	0.2449 (4)	0.2500	0.8784 (3)	0.0393 (8)
H9	0.1194	0.2500	0.8633	0.047*
C10	0.5314 (3)	0.2500	1.0167 (2)	0.0284 (6)
C11	0.6553 (4)	0.2500	1.1448 (3)	0.0429 (8)
H11	0.6135	0.2500	1.2197	0.051*
C12	0.8343 (4)	0.2500	1.1638 (3)	0.0398 (8)
H12	0.9169	0.2500	1.2513	0.048*
C13	0.8952 (4)	0.2500	1.0547 (3)	0.0631 (12)
H13	1.0201	0.2500	1.0674	0.076*
C14	0.7769 (4)	0.2500	0.9289 (3)	0.0889 (19)
H14	0.8209	0.2500	0.8551	0.107*
C15	0.5922 (3)	0.2500	0.9066 (3)	0.0378 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0199 (9)	0.0771 (16)	0.0236 (9)	0.000	0.0055 (7)	0.000
N1	0.0196 (11)	0.123 (3)	0.0224 (12)	0.000	0.0065 (9)	0.000
N2	0.0248 (12)	0.093 (2)	0.0270 (12)	0.000	0.0090 (9)	0.000
C1	0.0198 (14)	0.033 (2)	0.0229 (16)	0.0038 (12)	0.0051 (12)	0.0008 (12)
C2	0.057 (4)	0.056 (5)	0.031 (3)	0.004 (3)	0.018 (3)	0.002 (3)
C3	0.072 (3)	0.041 (3)	0.032 (2)	0.015 (2)	0.021 (2)	0.0047 (19)
C4	0.040 (2)	0.064 (4)	0.024 (2)	0.015 (2)	0.0142 (17)	0.002 (2)
C5	0.0231 (15)	0.054 (5)	0.0263 (17)	−0.0015 (15)	0.0075 (13)	0.0121 (16)
C6	0.0175 (15)	0.0301 (19)	0.039 (2)	−0.0008 (15)	−0.0015 (15)	0.0020 (17)
C7	0.055 (3)	0.037 (3)	0.054 (4)	−0.001 (3)	0.013 (3)	0.008 (3)
C8	0.0220 (12)	0.0435 (16)	0.0233 (12)	0.000	0.0053 (10)	0.000
C9	0.0188 (12)	0.069 (2)	0.0304 (14)	0.000	0.0084 (11)	0.000
C10	0.0230 (12)	0.0369 (15)	0.0259 (13)	0.000	0.0086 (10)	0.000
C11	0.0303 (14)	0.076 (2)	0.0227 (13)	0.000	0.0093 (11)	0.000
C12	0.0265 (14)	0.065 (2)	0.0243 (13)	0.000	0.0020 (11)	0.000
C13	0.0211 (14)	0.137 (4)	0.0291 (15)	0.000	0.0053 (12)	0.000
C14	0.0238 (15)	0.221 (6)	0.0247 (16)	0.000	0.0111 (13)	0.000
C15	0.0218 (13)	0.067 (2)	0.0236 (13)	0.000	0.0063 (10)	0.000

Geometric parameters (Å, º) top

O1—C8	1.359 (3)	C6—C7	1.472 (9)
O1—C1	1.420 (3)	C7—H7A	0.9800
O1—C1ⁱ	1.420 (3)	C7—H7B	0.9800
N1—C8	1.283 (3)	C7—H7C	0.9800
N1—C15	1.375 (3)	C8—C9	1.402 (4)
N2—C9	1.296 (4)	C9—H9	0.9500
N2—C10	1.369 (3)	C10—C15	1.392 (4)
C1—C2	1.3900	C10—C11	1.400 (4)
C1—C6	1.3900	C11—C12	1.360 (4)
C2—C3	1.3900	C11—H11	0.9500
C2—H2	0.9500	C12—C13	1.384 (4)
C3—C4	1.3900	C12—H12	0.9500
C3—H3	0.9500	C13—C14	1.365 (4)
C4—C5	1.3900	C13—H13	0.9500
C4—H4	0.9500	C14—C15	1.398 (4)
C5—C6	1.3900	C14—H14	0.9500
C5—H5	0.9500

C8—O1—C1	117.19 (19)	O1—C8—C9	114.4 (2)
C8—N1—C15	115.8 (2)	N2—C9—C8	122.2 (2)
C9—N2—C10	116.9 (2)	N2—C9—H9	118.9
C2—C1—C6	120.0	C8—C9—H9	118.9
C2—C1—O1	125.13 (17)	N2—C10—C15	120.2 (2)
C6—C1—O1	114.68 (17)	N2—C10—C11	120.2 (2)
C1—C2—C3	120.0	C15—C10—C11	119.6 (2)
C1—C2—H2	120.0	C12—C11—C10	121.2 (3)
C3—C2—H2	120.0	C12—C11—H11	119.4
C2—C3—C4	120.0	C10—C11—H11	119.4
C2—C3—H3	120.0	C11—C12—C13	119.4 (3)
C4—C3—H3	120.0	C11—C12—H12	120.3
C5—C4—C3	120.0	C13—C12—H12	120.3
C5—C4—H4	120.0	C14—C13—C12	120.4 (3)
C3—C4—H4	120.0	C14—C13—H13	119.8
C4—C5—C6	120.0	C12—C13—H13	119.8
C4—C5—H5	120.0	C13—C14—C15	121.3 (3)
C6—C5—H5	120.0	C13—C14—H14	119.4
C5—C6—C1	120.0	C15—C14—H14	119.4
C5—C6—C7	119.7 (3)	N1—C15—C10	121.5 (2)
C1—C6—C7	120.3 (3)	N1—C15—C14	120.4 (2)
N1—C8—O1	122.3 (2)	C10—C15—C14	118.1 (3)
N1—C8—C9	123.4 (2)

C8—O1—C1—C2	87.53 (18)	C1ⁱ—O1—C8—C9	160.91 (12)
C1ⁱ—O1—C1—C2	−173.48 (14)	C10—N2—C9—C8	0.000 (2)
C8—O1—C1—C6	−97.56 (16)	N1—C8—C9—N2	0.000 (2)
C1ⁱ—O1—C1—C6	1.43 (19)	O1—C8—C9—N2	180.000 (1)
C6—C1—C2—C3	0.0	C9—N2—C10—C15	0.000 (2)
O1—C1—C2—C3	174.7 (2)	C9—N2—C10—C11	180.000 (2)
C1—C2—C3—C4	0.0	N2—C10—C11—C12	180.000 (2)
C2—C3—C4—C5	0.0	C15—C10—C11—C12	0.000 (2)
C3—C4—C5—C6	0.0	C10—C11—C12—C13	0.000 (2)
C4—C5—C6—C1	0.0	C11—C12—C13—C14	0.000 (2)
C4—C5—C6—C7	−178.3 (4)	C12—C13—C14—C15	0.000 (2)
C2—C1—C6—C5	0.0	C8—N1—C15—C10	0.000 (1)
O1—C1—C6—C5	−175.2 (2)	C8—N1—C15—C14	180.000 (1)
C2—C1—C6—C7	178.2 (4)	N2—C10—C15—N1	0.000 (2)
O1—C1—C6—C7	3.0 (4)	C11—C10—C15—N1	180.000 (1)
C15—N1—C8—O1	180.000 (1)	N2—C10—C15—C14	180.000 (2)
C15—N1—C8—C9	0.000 (1)	C11—C10—C15—C14	0.000 (2)
C1—O1—C8—N1	19.09 (12)	C13—C14—C15—N1	180.000 (2)
C1ⁱ—O1—C8—N1	−19.09 (12)	C13—C14—C15—C10	0.000 (2)
C1—O1—C8—C9	−160.91 (12)

Symmetry code: (i) x, −y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂N₂O
M_r	236.27
Crystal system, space group	Monoclinic, P2₁/m
Temperature (K)	100
a, b, c (Å)	7.874 (2), 7.413 (1), 10.596 (2)
β (°)	108.332 (3)
V (Å³)	587.1 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.20 × 0.08

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3392, 1443, 1032
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.183, 1.03
No. of reflections	1443
No. of parameters	119
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.31

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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