Quinoxalin-2-yl m-tolyl ether

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

doi:10.1107/S1600536808026822

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1822

doi:10.1107/S1600536808026822

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Quinoxalin-2-yl m-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 79.4 (1)°. The angle at the O atom is widened to 116.93 (9)°.

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, C 2/c
a = 18.5958 (5) Å
b = 7.0710 (1) Å
c = 19.4821 (5) Å
β = 112.487 (1)°
V = 2366.94 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 (2) K
0.40 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
8036 measured reflections
2708 independent reflections
2179 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.112
S = 1.04
2708 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.26 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/S1600536808026822/bt2770sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808026822/bt2770Isup2.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

m-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) of C₁₅H₁₂N₂O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Quinoxalin-2-yl m-tolyl ether top

Crystal data top

C₁₅H₁₂N₂O	F(000) = 992
M_r = 236.27	D_x = 1.326 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 756 reflections
a = 18.5958 (5) Å	θ = 2.7–24.6°
b = 7.0710 (1) Å	µ = 0.09 mm⁻¹
c = 19.4821 (5) Å	T = 100 K
β = 112.487 (1)°	Block, colorless
V = 2366.94 (9) Å³	0.40 × 0.15 × 0.10 mm
Z = 8

Data collection top

Bruker SMART APEX diffractometer	2179 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 27.5°, θ_min = 2.3°
ω scans	h = −24→24
8036 measured reflections	k = −9→9
2708 independent reflections	l = −25→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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0586P)² + 1.0233P] where P = (F_o² + 2F_c²)/3
2708 reflections	(Δ/σ)_max = 0.001
164 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₅H₁₂N₂O	V = 2366.94 (9) Å³
M_r = 236.27	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 18.5958 (5) Å	µ = 0.09 mm⁻¹
b = 7.0710 (1) Å	T = 100 K
c = 19.4821 (5) Å	0.40 × 0.15 × 0.10 mm
β = 112.487 (1)°

Data collection top

Bruker SMART APEX diffractometer	2179 reflections with I > 2σ(I)
8036 measured reflections	R_int = 0.025
2708 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.04	Δρ_max = 0.29 e Å⁻³
2708 reflections	Δρ_min = −0.26 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	0.67552 (5)	0.84219 (13)	0.54655 (5)	0.0215 (2)
N1	0.58519 (6)	0.74119 (14)	0.59395 (5)	0.0174 (2)
N2	0.47213 (6)	0.77607 (15)	0.44719 (6)	0.0200 (2)
C1	0.73297 (7)	0.83475 (17)	0.61927 (7)	0.0179 (3)
C2	0.78445 (7)	0.68518 (17)	0.63734 (7)	0.0202 (3)
H2	0.7802	0.5894	0.6018	0.024*
C3	0.84288 (7)	0.67583 (18)	0.70839 (7)	0.0223 (3)
C4	0.84907 (7)	0.82240 (19)	0.75792 (7)	0.0215 (3)
H4	0.8893	0.8193	0.8060	0.026*
C5	0.79743 (7)	0.97296 (18)	0.73822 (7)	0.0220 (3)
H5	0.8027	1.0723	0.7727	0.026*
C6	0.73806 (7)	0.97912 (17)	0.66841 (7)	0.0206 (3)
H6	0.7018	1.0804	0.6548	0.025*
C7	0.89521 (8)	0.5050 (2)	0.73175 (9)	0.0364 (4)
H7A	0.9393	0.5328	0.7781	0.055*
H7B	0.9145	0.4736	0.6929	0.055*
H7C	0.8658	0.3977	0.7395	0.055*
C8	0.60151 (7)	0.79686 (16)	0.53826 (7)	0.0174 (3)
C9	0.54531 (7)	0.81523 (17)	0.46401 (7)	0.0192 (3)
H9	0.5618	0.8570	0.4260	0.023*
C10	0.45167 (7)	0.71606 (16)	0.50459 (7)	0.0176 (3)
C11	0.37355 (7)	0.66926 (17)	0.48997 (7)	0.0218 (3)
H11	0.3356	0.6792	0.4408	0.026*
C12	0.35219 (7)	0.60961 (18)	0.54625 (7)	0.0230 (3)
H12	0.2994	0.5791	0.5362	0.028*
C13	0.40826 (7)	0.59334 (17)	0.61903 (7)	0.0219 (3)
H13	0.3930	0.5512	0.6577	0.026*
C14	0.48469 (7)	0.63759 (17)	0.63472 (7)	0.0194 (3)
H14	0.5219	0.6266	0.6841	0.023*
C15	0.50814 (7)	0.69927 (16)	0.57774 (7)	0.0163 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0167 (4)	0.0313 (5)	0.0162 (4)	−0.0030 (4)	0.0059 (3)	0.0016 (4)
N1	0.0173 (5)	0.0183 (5)	0.0161 (5)	0.0006 (4)	0.0057 (4)	0.0004 (4)
N2	0.0221 (6)	0.0191 (5)	0.0168 (5)	−0.0012 (4)	0.0051 (4)	0.0003 (4)
C1	0.0150 (6)	0.0236 (6)	0.0156 (6)	−0.0040 (5)	0.0063 (5)	0.0018 (5)
C2	0.0197 (6)	0.0207 (6)	0.0228 (6)	−0.0035 (5)	0.0108 (5)	−0.0027 (5)
C3	0.0173 (6)	0.0252 (6)	0.0266 (7)	0.0009 (5)	0.0106 (5)	0.0046 (5)
C4	0.0160 (6)	0.0301 (7)	0.0176 (6)	−0.0044 (5)	0.0055 (5)	0.0027 (5)
C5	0.0240 (7)	0.0248 (6)	0.0201 (6)	−0.0051 (5)	0.0116 (5)	−0.0028 (5)
C6	0.0203 (6)	0.0213 (6)	0.0223 (6)	0.0011 (5)	0.0104 (5)	0.0017 (5)
C7	0.0294 (8)	0.0366 (8)	0.0422 (9)	0.0122 (6)	0.0127 (7)	0.0077 (7)
C8	0.0167 (6)	0.0168 (6)	0.0190 (6)	0.0001 (4)	0.0071 (5)	−0.0010 (5)
C9	0.0220 (7)	0.0197 (6)	0.0161 (6)	−0.0009 (5)	0.0076 (5)	0.0005 (5)
C10	0.0194 (6)	0.0141 (5)	0.0186 (6)	0.0004 (4)	0.0065 (5)	−0.0001 (5)
C11	0.0180 (6)	0.0209 (6)	0.0218 (6)	−0.0007 (5)	0.0023 (5)	0.0011 (5)
C12	0.0178 (6)	0.0227 (6)	0.0291 (7)	−0.0027 (5)	0.0097 (5)	−0.0005 (5)
C13	0.0251 (7)	0.0200 (6)	0.0237 (6)	−0.0011 (5)	0.0128 (5)	0.0004 (5)
C14	0.0213 (6)	0.0190 (6)	0.0180 (6)	0.0003 (5)	0.0074 (5)	0.0003 (5)
C15	0.0178 (6)	0.0133 (5)	0.0172 (6)	0.0010 (4)	0.0060 (5)	−0.0016 (4)

Geometric parameters (Å, º) top

O1—C8	1.3612 (14)	C6—H6	0.9500
O1—C1	1.4119 (14)	C7—H7A	0.9800
N1—C8	1.2947 (16)	C7—H7B	0.9800
N1—C15	1.3764 (15)	C7—H7C	0.9800
N2—C9	1.3018 (15)	C8—C9	1.4302 (17)
N2—C10	1.3787 (16)	C9—H9	0.9500
C1—C6	1.3778 (17)	C10—C11	1.4087 (17)
C1—C2	1.3787 (17)	C10—C15	1.4153 (16)
C2—C3	1.3967 (17)	C11—C12	1.3678 (18)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.3905 (19)	C12—C13	1.4071 (18)
C3—C7	1.5080 (18)	C12—H12	0.9500
C4—C5	1.3859 (18)	C13—C14	1.3707 (17)
C4—H4	0.9500	C13—H13	0.9500
C5—C6	1.3863 (17)	C14—C15	1.4082 (17)
C5—H5	0.9500	C14—H14	0.9500

C8—O1—C1	116.93 (9)	H7B—C7—H7C	109.5
C8—N1—C15	115.49 (10)	N1—C8—O1	121.51 (11)
C9—N2—C10	116.58 (10)	N1—C8—C9	124.08 (11)
C6—C1—C2	122.30 (11)	O1—C8—C9	114.41 (10)
C6—C1—O1	119.61 (11)	N2—C9—C8	121.63 (11)
C2—C1—O1	118.02 (11)	N2—C9—H9	119.2
C1—C2—C3	119.36 (11)	C8—C9—H9	119.2
C1—C2—H2	120.3	N2—C10—C11	119.44 (11)
C3—C2—H2	120.3	N2—C10—C15	120.93 (11)
C4—C3—C2	118.62 (11)	C11—C10—C15	119.63 (11)
C4—C3—C7	121.00 (12)	C12—C11—C10	120.23 (12)
C2—C3—C7	120.30 (12)	C12—C11—H11	119.9
C5—C4—C3	121.04 (11)	C10—C11—H11	119.9
C5—C4—H4	119.5	C11—C12—C13	120.17 (12)
C3—C4—H4	119.5	C11—C12—H12	119.9
C6—C5—C4	120.22 (12)	C13—C12—H12	119.9
C6—C5—H5	119.9	C14—C13—C12	120.76 (12)
C4—C5—H5	119.9	C14—C13—H13	119.6
C1—C6—C5	118.40 (12)	C12—C13—H13	119.6
C1—C6—H6	120.8	C13—C14—C15	120.15 (11)
C5—C6—H6	120.8	C13—C14—H14	119.9
C3—C7—H7A	109.5	C15—C14—H14	119.9
C3—C7—H7B	109.5	N1—C15—C14	119.66 (11)
H7A—C7—H7B	109.5	N1—C15—C10	121.29 (11)
C3—C7—H7C	109.5	C14—C15—C10	119.05 (11)
H7A—C7—H7C	109.5

C8—O1—C1—C6	−77.38 (14)	N1—C8—C9—N2	−0.01 (19)
C8—O1—C1—C2	105.36 (13)	O1—C8—C9—N2	179.64 (11)
C6—C1—C2—C3	1.58 (18)	C9—N2—C10—C11	−179.26 (11)
O1—C1—C2—C3	178.76 (10)	C9—N2—C10—C15	0.17 (17)
C1—C2—C3—C4	−2.44 (18)	N2—C10—C11—C12	−179.95 (11)
C1—C2—C3—C7	174.40 (12)	C15—C10—C11—C12	0.61 (18)
C2—C3—C4—C5	1.48 (18)	C10—C11—C12—C13	−0.45 (19)
C7—C3—C4—C5	−175.34 (12)	C11—C12—C13—C14	0.31 (19)
C3—C4—C5—C6	0.41 (18)	C12—C13—C14—C15	−0.33 (19)
C2—C1—C6—C5	0.31 (18)	C8—N1—C15—C14	−179.98 (11)
O1—C1—C6—C5	−176.82 (10)	C8—N1—C15—C10	0.31 (16)
C4—C5—C6—C1	−1.31 (18)	C13—C14—C15—N1	−179.24 (11)
C15—N1—C8—O1	−179.77 (10)	C13—C14—C15—C10	0.48 (18)
C15—N1—C8—C9	−0.15 (17)	N2—C10—C15—N1	−0.33 (17)
C1—O1—C8—N1	−3.05 (16)	C11—C10—C15—N1	179.09 (11)
C1—O1—C8—C9	177.29 (10)	N2—C10—C15—C14	179.95 (11)
C10—N2—C9—C8	0.00 (17)	C11—C10—C15—C14	−0.62 (17)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂N₂O
M_r	236.27
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	18.5958 (5), 7.0710 (1), 19.4821 (5)
β (°)	112.487 (1)
V (Å³)	2366.94 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8036, 2708, 2179
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.112, 1.04
No. of reflections	2708
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.26

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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