Quinoxalin-2-yl m-tolyl ether

Abstract

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,

• a = 18.5958 (5) Å

• b = 7.0710 (1) Å

• c = 19.4821 (5) Å

• β = 112.487 (1)°

• V = 2366.94 (9) ų

• 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[F ² > 2σ(F ²)] = 0.040

• wR(F ²) = 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 ▶).

Supplementary Material

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

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Experimental

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.

Refinement

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).

Figures

Fig. 1.

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

Crystal data

C15H12N2O	F000 = 992
Mr = 236.27	Dx = 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 = 2.7–24.6º
b = 7.0710 (1) Å	µ = 0.09 mm−1
c = 19.4821 (5) Å	T = 100 (2) K
β = 112.487 (1)º	Block, colorless
V = 2366.94 (9) Å3	0.40 × 0.15 × 0.10 mm
Z = 8

Data collection

Bruker SMART APEX diffractometer	2179 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
Monochromator: graphite	θmax = 27.5º
T = 100(2) K	θmin = 2.3º
ω scans	h = −24→24
Absorption correction: None	k = −9→9
8036 measured reflections	l = −25→25
2708 independent reflections

Refinement

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.0586P)2 + 1.0233P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2708 reflections	Δρmax = 0.29 e Å−3
164 parameters	Δρmin = −0.26 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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)