2-Naphthyl quinoxalin-2-yl ether

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

doi:10.1107/S1600536809007855

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o732

doi:10.1107/S1600536809007855

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2-Naphthyl quinoxalin-2-yl ether

Noor Doha 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 2 March 2009; accepted 4 March 2009; online 11 March 2009)

In the crystal structure of the title compound, C₁₈H₁₂N₂O, the two fused rings are aligned at 64.2 (1)°; the C—O—C angle is 118.73 (12)°.

Related literature

For the crystal structure of 1-naphthyl quinoxalinyl ether, see: Hassan et al. (2009 ).

Experimental

Crystal data

C₁₈H₁₂N₂O
M_r = 272.30
Monoclinic, P 2₁ /c
a = 6.808 (1) Å
b = 7.609 (1) Å
c = 26.234 (3) Å
β = 92.522 (2)°
V = 1357.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.45 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
7510 measured reflections
3094 independent reflections
1950 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.127
S = 1.04
3094 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.16 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007855/tk2387sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809007855/tk2387Isup2.hkl

checkCIF report

Related literature top

For the crystal structure of 1-naphthyl quinoxalinyl ether, see: Hassan et al. (2009).

Experimental top

2-Naphthol (2.88 g, 20 mmol) was mixed with sodium hydroxide (0.08 g, 20 mmol) in several drops of water. The water was then evaporated. The paste was heated with 2-chloroquinoxaline (3.29 g, 20 mmol) at 423–433 K for 6 h. The product was dissolved in water and the solution extracted with chloroform. The chloroform phase was dried over sodium sulfate; the evaporation of the solvent gave a product that was recrystallized from an ethyl acetate/hexane.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the molecule of C₁₈H₁₂N₂O at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

2-Naphthyl quinoxalin-2-yl ether top

Crystal data top

C₁₈H₁₂N₂O	F(000) = 568
M_r = 272.30	D_x = 1.332 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1541 reflections
a = 6.808 (1) Å	θ = 2.7–28.2°
b = 7.609 (1) Å	µ = 0.08 mm⁻¹
c = 26.234 (3) Å	T = 295 K
β = 92.522 (2)°	Block, colorless
V = 1357.5 (3) Å³	0.45 × 0.15 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	1950 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 27.5°, θ_min = 2.8°
ω scans	h = −6→8
7510 measured reflections	k = −9→8
3094 independent reflections	l = −28→34

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0544P)² + 0.1253P] where P = (F_o² + 2F_c²)/3
3094 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₈H₁₂N₂O	V = 1357.5 (3) Å³
M_r = 272.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.808 (1) Å	µ = 0.08 mm⁻¹
b = 7.609 (1) Å	T = 295 K
c = 26.234 (3) Å	0.45 × 0.15 × 0.10 mm
β = 92.522 (2)°

Data collection top

Bruker SMART APEX diffractometer	1950 reflections with I > 2σ(I)
7510 measured reflections	R_int = 0.032
3094 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.04	Δρ_max = 0.17 e Å⁻³
3094 reflections	Δρ_min = −0.16 e Å⁻³
190 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.11303 (15)	0.36756 (17)	0.59259 (4)	0.0477 (3)
N1	−0.13352 (19)	0.2389 (2)	0.47654 (5)	0.0459 (4)
N2	0.25074 (18)	0.24104 (18)	0.52218 (5)	0.0379 (3)
C1	0.2995 (2)	0.3759 (2)	0.61786 (6)	0.0392 (4)
C2	0.4441 (2)	0.4866 (2)	0.59948 (6)	0.0447 (4)
H2	0.4210	0.5499	0.5695	0.054*
C3	0.6192 (2)	0.5003 (2)	0.62616 (6)	0.0435 (4)
H3	0.7168	0.5723	0.6138	0.052*
C4	0.6559 (2)	0.4077 (2)	0.67216 (6)	0.0371 (4)
C5	0.5053 (2)	0.3003 (2)	0.69082 (6)	0.0394 (4)
C6	0.3253 (2)	0.2858 (2)	0.66207 (6)	0.0412 (4)
H6	0.2253	0.2147	0.6735	0.049*
C7	0.8364 (2)	0.4201 (3)	0.70077 (6)	0.0483 (5)
H7	0.9372	0.4892	0.6888	0.058*
C8	0.8642 (3)	0.3322 (3)	0.74553 (7)	0.0618 (6)
H8	0.9839	0.3414	0.7638	0.074*
C9	0.7154 (3)	0.2285 (3)	0.76428 (7)	0.0694 (6)
H9	0.7355	0.1704	0.7953	0.083*
C10	0.5402 (3)	0.2116 (3)	0.73751 (7)	0.0593 (5)
H10	0.4424	0.1406	0.7502	0.071*
C11	0.0985 (2)	0.3003 (2)	0.54445 (6)	0.0375 (4)
C12	−0.0954 (2)	0.2999 (2)	0.52209 (6)	0.0439 (4)
H12	−0.1976	0.3445	0.5406	0.053*
C13	0.0233 (2)	0.1738 (2)	0.45104 (6)	0.0389 (4)
C14	−0.0076 (3)	0.1015 (3)	0.40208 (6)	0.0520 (5)
H14	−0.1333	0.1008	0.3867	0.062*
C15	0.1453 (3)	0.0325 (3)	0.37707 (7)	0.0561 (5)
H15	0.1237	−0.0157	0.3447	0.067*
C16	0.3351 (3)	0.0340 (2)	0.39983 (7)	0.0524 (5)
H16	0.4385	−0.0139	0.3824	0.063*
C17	0.3705 (2)	0.1044 (2)	0.44705 (6)	0.0430 (4)
H17	0.4977	0.1063	0.4615	0.052*
C18	0.2149 (2)	0.1739 (2)	0.47388 (5)	0.0348 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0342 (6)	0.0636 (9)	0.0449 (6)	0.0032 (5)	−0.0035 (5)	−0.0096 (6)
N1	0.0344 (8)	0.0508 (10)	0.0517 (8)	−0.0015 (6)	−0.0080 (6)	0.0037 (7)
N2	0.0336 (7)	0.0387 (8)	0.0409 (7)	−0.0003 (6)	−0.0048 (5)	0.0016 (6)
C1	0.0348 (9)	0.0424 (11)	0.0402 (9)	0.0010 (7)	−0.0013 (7)	−0.0076 (7)
C2	0.0497 (10)	0.0453 (11)	0.0389 (9)	−0.0025 (8)	−0.0017 (7)	0.0046 (8)
C3	0.0441 (9)	0.0424 (11)	0.0441 (9)	−0.0095 (8)	0.0033 (7)	0.0009 (8)
C4	0.0376 (8)	0.0339 (10)	0.0398 (8)	0.0010 (7)	0.0004 (6)	−0.0055 (7)
C5	0.0420 (9)	0.0356 (10)	0.0404 (9)	0.0010 (7)	0.0010 (7)	0.0008 (7)
C6	0.0392 (9)	0.0390 (11)	0.0457 (9)	−0.0056 (7)	0.0052 (7)	−0.0005 (8)
C7	0.0382 (9)	0.0534 (13)	0.0529 (10)	−0.0002 (8)	−0.0015 (7)	−0.0099 (9)
C8	0.0510 (12)	0.0723 (16)	0.0603 (12)	0.0077 (10)	−0.0177 (9)	−0.0017 (10)
C9	0.0681 (15)	0.0816 (17)	0.0571 (12)	0.0052 (12)	−0.0130 (10)	0.0210 (11)
C10	0.0594 (12)	0.0617 (15)	0.0566 (11)	−0.0039 (10)	−0.0004 (9)	0.0194 (10)
C11	0.0366 (9)	0.0351 (10)	0.0404 (8)	−0.0013 (7)	−0.0033 (7)	0.0026 (7)
C12	0.0332 (8)	0.0476 (11)	0.0506 (10)	0.0030 (8)	−0.0019 (7)	0.0007 (8)
C13	0.0387 (9)	0.0341 (10)	0.0431 (9)	−0.0050 (7)	−0.0058 (7)	0.0045 (7)
C14	0.0502 (11)	0.0557 (13)	0.0486 (10)	−0.0079 (9)	−0.0138 (8)	−0.0009 (9)
C15	0.0689 (13)	0.0558 (14)	0.0431 (10)	−0.0075 (10)	−0.0046 (9)	−0.0087 (9)
C16	0.0559 (11)	0.0509 (13)	0.0507 (10)	0.0038 (9)	0.0047 (8)	−0.0040 (9)
C17	0.0401 (9)	0.0415 (11)	0.0473 (9)	0.0018 (7)	−0.0013 (7)	0.0025 (8)
C18	0.0360 (8)	0.0295 (9)	0.0386 (8)	−0.0029 (7)	−0.0036 (6)	0.0060 (7)

Geometric parameters (Å, º) top

O1—C11	1.3622 (18)	C7—H7	0.9300
O1—C1	1.4073 (18)	C8—C9	1.391 (3)
N1—C12	1.297 (2)	C8—H8	0.9300
N1—C13	1.377 (2)	C9—C10	1.363 (3)
N2—C11	1.2928 (19)	C9—H9	0.9300
N2—C18	1.3778 (19)	C10—H10	0.9300
C1—C6	1.352 (2)	C11—C12	1.421 (2)
C1—C2	1.398 (2)	C12—H12	0.9300
C2—C3	1.359 (2)	C13—C14	1.405 (2)
C2—H2	0.9300	C13—C18	1.411 (2)
C3—C4	1.410 (2)	C14—C15	1.360 (3)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.415 (2)	C15—C16	1.399 (2)
C4—C7	1.415 (2)	C15—H15	0.9300
C5—C10	1.410 (2)	C16—C17	1.361 (2)
C5—C6	1.414 (2)	C16—H16	0.9300
C6—H6	0.9300	C17—C18	1.401 (2)
C7—C8	1.357 (2)	C17—H17	0.9300

C11—O1—C1	118.73 (12)	C8—C9—H9	119.8
C12—N1—C13	116.62 (13)	C9—C10—C5	120.83 (19)
C11—N2—C18	115.58 (13)	C9—C10—H10	119.6
C6—C1—C2	122.30 (15)	C5—C10—H10	119.6
C6—C1—O1	117.50 (15)	N2—C11—O1	121.55 (13)
C2—C1—O1	119.95 (14)	N2—C11—C12	124.14 (15)
C3—C2—C1	118.92 (15)	O1—C11—C12	114.31 (14)
C3—C2—H2	120.5	N1—C12—C11	121.72 (15)
C1—C2—H2	120.5	N1—C12—H12	119.1
C2—C3—C4	121.39 (16)	C11—C12—H12	119.1
C2—C3—H3	119.3	N1—C13—C14	119.82 (15)
C4—C3—H3	119.3	N1—C13—C18	121.02 (14)
C3—C4—C5	118.72 (14)	C14—C13—C18	119.14 (15)
C3—C4—C7	122.55 (16)	C15—C14—C13	120.36 (16)
C5—C4—C7	118.72 (15)	C15—C14—H14	119.8
C10—C5—C4	118.70 (15)	C13—C14—H14	119.8
C10—C5—C6	122.33 (16)	C14—C15—C16	120.19 (16)
C4—C5—C6	118.97 (14)	C14—C15—H15	119.9
C1—C6—C5	119.65 (15)	C16—C15—H15	119.9
C1—C6—H6	120.2	C17—C16—C15	120.98 (17)
C5—C6—H6	120.2	C17—C16—H16	119.5
C8—C7—C4	120.72 (17)	C15—C16—H16	119.5
C8—C7—H7	119.6	C16—C17—C18	119.89 (16)
C4—C7—H7	119.6	C16—C17—H17	120.1
C7—C8—C9	120.65 (17)	C18—C17—H17	120.1
C7—C8—H8	119.7	N2—C18—C17	119.67 (14)
C9—C8—H8	119.7	N2—C18—C13	120.91 (14)
C10—C9—C8	120.38 (18)	C17—C18—C13	119.43 (14)
C10—C9—H9	119.8

C11—O1—C1—C6	−119.60 (16)	C18—N2—C11—O1	178.93 (14)
C11—O1—C1—C2	65.9 (2)	C18—N2—C11—C12	−0.3 (2)
C6—C1—C2—C3	2.0 (3)	C1—O1—C11—N2	1.5 (2)
O1—C1—C2—C3	176.20 (15)	C1—O1—C11—C12	−179.20 (15)
C1—C2—C3—C4	−1.1 (3)	C13—N1—C12—C11	0.3 (2)
C2—C3—C4—C5	−0.7 (2)	N2—C11—C12—N1	−0.2 (3)
C2—C3—C4—C7	−179.77 (16)	O1—C11—C12—N1	−179.53 (15)
C3—C4—C5—C10	−178.29 (16)	C12—N1—C13—C14	178.37 (16)
C7—C4—C5—C10	0.8 (2)	C12—N1—C13—C18	0.1 (2)
C3—C4—C5—C6	1.7 (2)	N1—C13—C14—C15	−178.25 (17)
C7—C4—C5—C6	−179.25 (15)	C18—C13—C14—C15	0.0 (3)
C2—C1—C6—C5	−1.1 (3)	C13—C14—C15—C16	−0.4 (3)
O1—C1—C6—C5	−175.37 (14)	C14—C15—C16—C17	−0.2 (3)
C10—C5—C6—C1	179.15 (16)	C15—C16—C17—C18	1.1 (3)
C4—C5—C6—C1	−0.8 (2)	C11—N2—C18—C17	−179.07 (14)
C3—C4—C7—C8	178.35 (17)	C11—N2—C18—C13	0.8 (2)
C5—C4—C7—C8	−0.7 (3)	C16—C17—C18—N2	178.38 (15)
C4—C7—C8—C9	−0.2 (3)	C16—C17—C18—C13	−1.5 (2)
C7—C8—C9—C10	1.0 (3)	N1—C13—C18—N2	−0.7 (2)
C8—C9—C10—C5	−0.9 (3)	C14—C13—C18—N2	−178.94 (15)
C4—C5—C10—C9	0.0 (3)	N1—C13—C18—C17	179.13 (15)
C6—C5—C10—C9	−179.97 (18)	C14—C13—C18—C17	0.9 (2)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₂N₂O
M_r	272.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	6.808 (1), 7.609 (1), 26.234 (3)
β (°)	92.522 (2)
V (Å³)	1357.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.45 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7510, 3094, 1950
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.127, 1.04
No. of reflections	3094
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.16

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

We thank the University of Malaya for supporting this study (FS358/2008 A).

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hassan, N. D., Tajuddin, H. A., Abdullah, Z. & Ng, S. W. (2009). Acta Cryst. E65, o731. Web of Science CSD CrossRef IUCr Journals Google Scholar
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