Quinoxalin-2-yl p-tolyl ether.

The dihedral angle between the two aromatic ring systems in the title compound, C(15)H(12)N(2)O, 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 = 236.27

Triclinic,

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[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.099

S = 0.99

2030 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026834/bt2771sup1.cif

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

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

C15H12N2O	Z = 2
Mr = 236.27	F000 = 248
Triclinic, P1	Dx = 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 = 2.3–28.3º
c = 12.8112 (2) Å	µ = 0.09 mm−1
α = 74.660 (1)º	T = 100 (2) K
β = 81.163 (1)º	Irregular block, colorless
γ = 89.095 (1)º	0.25 × 0.25 × 0.25 mm
V = 589.35 (2) Å3

Bruker SMART APEX diffractometer	1764 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.012
Monochromator: graphite	θmax = 25.0º
ω scans	θmin = 2.3º
Absorption correction: None	h = −6→6
2828 measured reflections	k = −7→10
2030 independent reflections	l = −15→15

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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.099	w = 1/[σ2(Fo2) + (0.0589P)2 + 0.1439P] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
2030 reflections	Δρmax = 0.15 e Å−3
164 parameters	Δρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
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*

	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)

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)