Quinoxalin-2-yl m-tolyl ether.

The dihedral angle between the two aromatic ring systems in the title compound, C(15)H(12)N(2)O, 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 = 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) 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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.112

S = 1.04

2708 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026822/bt2770sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026822/bt2770Isup2.hkl

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

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

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 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

	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)

	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)

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)