Literature DB >> 21201796

Quinoxalin-2-yl o-tolyl ether.

Nor Duha Hassan¹, Hairul Anuar Tajuddin, Zanariah Abdullah, Seik Weng Ng.

Abstract

The dihedral angle between the two aromatic ring systems in the title compound, C(15)H(12)N(2)O, is 85.9 (1)°; The angle at the O atom is widened to 118.2 (2)°. The quinoxalin-yloxy part of the mol-ecule lies on a mirror plane and the tolyl group is disordered over two positions about the mirror plane.

Entities: Chemical Disease Species

Year: 2008 PMID： 21201796 PMCID： PMC2960597 DOI： 10.1107/S1600536808026810

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

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 = 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[F 2 > 2σ(F 2)] = 0.065 wR(F 2) = 0.183 S = 1.03 1443 reflections 119 parameters H-atom parameters constrained Δρmax = 0.24 e Å−3 Δρmin = −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 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026810/bt2769sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026810/bt2769Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₅H₁₂N₂O	F₀₀₀ = 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 = 2.7–24.6º
b = 7.413 (1) Å	µ = 0.09 mm⁻¹
c = 10.596 (2) Å	T = 100 (2) K
β = 108.332 (3)º	Block, colorless
V = 587.1 (2) Å³	0.20 × 0.20 × 0.08 mm
Z = 2

Bruker SMART APEX diffractometer	1032 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
Monochromator: graphite	θ_max = 27.5º
T = 100(2) K	θ_min = 2.0º
ω scans	h = −10→8
Absorption correction: None	k = −9→8
3392 measured reflections	l = −12→13
1443 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)] = 0.065	H-atom parameters constrained
wR(F²) = 0.183	w = 1/[σ²(F_o²) + (0.0776P)² + 0.4106P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
1443 reflections	Δρ_max = 0.24 e Å⁻³
119 parameters	Δρ_min = −0.31 e Å⁻³
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	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)

	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

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)

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