supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

Acta Cryst. (2009). E65, o732    [ doi:10.1107/S1600536809007855 ]

2-Naphthyl quinoxalin-2-yl ether

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

Abstract top

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 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.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C).

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
[Figure 1] 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
C18H12N2OF(000) = 568
Mr = 272.30Dx = 1.332 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1541 reflections
a = 6.808 (1) Åθ = 2.7–28.2°
b = 7.609 (1) ŵ = 0.08 mm−1
c = 26.234 (3) ÅT = 295 K
β = 92.522 (2)°Block, colorless
V = 1357.5 (3) Å30.45 × 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 tubeRint = 0.032
graphiteθmax = 27.5°, θmin = 2.8°
ω scansh = −6→8
7510 measured reflectionsk = −9→8
3094 independent reflectionsl = −28→34
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0544P)2 + 0.1253P]
where P = (Fo2 + 2Fc2)/3
3094 reflections(Δ/σ)max = 0.001
190 parametersΔρmax = 0.17 e Å−3
0 restraintsΔρmin = −0.16 e Å−3
Crystal data top
C18H12N2OV = 1357.5 (3) Å3
Mr = 272.30Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.808 (1) ŵ = 0.08 mm−1
b = 7.609 (1) ÅT = 295 K
c = 26.234 (3) Å0.45 × 0.15 × 0.10 mm
β = 92.522 (2)°
Data collection top
Bruker SMART APEX
diffractometer		1950 reflections with I > 2σ(I)
7510 measured reflectionsRint = 0.032
3094 independent reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.127Δρmax = 0.17 e Å−3
S = 1.04Δρmin = −0.16 e Å−3
3094 reflectionsAbsolute structure: ?
190 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.11303 (15)0.36756 (17)0.59259 (4)0.0477 (3)
N1−0.13352 (19)0.2389 (2)0.47654 (5)0.0459 (4)
N20.25074 (18)0.24104 (18)0.52218 (5)0.0379 (3)
C10.2995 (2)0.3759 (2)0.61786 (6)0.0392 (4)
C20.4441 (2)0.4866 (2)0.59948 (6)0.0447 (4)
H20.42100.54990.56950.054*
C30.6192 (2)0.5003 (2)0.62616 (6)0.0435 (4)
H30.71680.57230.61380.052*
C40.6559 (2)0.4077 (2)0.67216 (6)0.0371 (4)
C50.5053 (2)0.3003 (2)0.69082 (6)0.0394 (4)
C60.3253 (2)0.2858 (2)0.66207 (6)0.0412 (4)
H60.22530.21470.67350.049*
C70.8364 (2)0.4201 (3)0.70077 (6)0.0483 (5)
H70.93720.48920.68880.058*
C80.8642 (3)0.3322 (3)0.74553 (7)0.0618 (6)
H80.98390.34140.76380.074*
C90.7154 (3)0.2285 (3)0.76428 (7)0.0694 (6)
H90.73550.17040.79530.083*
C100.5402 (3)0.2116 (3)0.73751 (7)0.0593 (5)
H100.44240.14060.75020.071*
C110.0985 (2)0.3003 (2)0.54445 (6)0.0375 (4)
C12−0.0954 (2)0.2999 (2)0.52209 (6)0.0439 (4)
H12−0.19760.34450.54060.053*
C130.0233 (2)0.1738 (2)0.45104 (6)0.0389 (4)
C14−0.0076 (3)0.1015 (3)0.40208 (6)0.0520 (5)
H14−0.13330.10080.38670.062*
C150.1453 (3)0.0325 (3)0.37707 (7)0.0561 (5)
H150.1237−0.01570.34470.067*
C160.3351 (3)0.0340 (2)0.39983 (7)0.0524 (5)
H160.4385−0.01390.38240.063*
C170.3705 (2)0.1044 (2)0.44705 (6)0.0430 (4)
H170.49770.10630.46150.052*
C180.2149 (2)0.1739 (2)0.47388 (5)0.0348 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0342 (6)0.0636 (9)0.0449 (6)0.0032 (5)−0.0035 (5)−0.0096 (6)
N10.0344 (8)0.0508 (10)0.0517 (8)−0.0015 (6)−0.0080 (6)0.0037 (7)
N20.0336 (7)0.0387 (8)0.0409 (7)−0.0003 (6)−0.0048 (5)0.0016 (6)
C10.0348 (9)0.0424 (11)0.0402 (9)0.0010 (7)−0.0013 (7)−0.0076 (7)
C20.0497 (10)0.0453 (11)0.0389 (9)−0.0025 (8)−0.0017 (7)0.0046 (8)
C30.0441 (9)0.0424 (11)0.0441 (9)−0.0095 (8)0.0033 (7)0.0009 (8)
C40.0376 (8)0.0339 (10)0.0398 (8)0.0010 (7)0.0004 (6)−0.0055 (7)
C50.0420 (9)0.0356 (10)0.0404 (9)0.0010 (7)0.0010 (7)0.0008 (7)
C60.0392 (9)0.0390 (11)0.0457 (9)−0.0056 (7)0.0052 (7)−0.0005 (8)
C70.0382 (9)0.0534 (13)0.0529 (10)−0.0002 (8)−0.0015 (7)−0.0099 (9)
C80.0510 (12)0.0723 (16)0.0603 (12)0.0077 (10)−0.0177 (9)−0.0017 (10)
C90.0681 (15)0.0816 (17)0.0571 (12)0.0052 (12)−0.0130 (10)0.0210 (11)
C100.0594 (12)0.0617 (15)0.0566 (11)−0.0039 (10)−0.0004 (9)0.0194 (10)
C110.0366 (9)0.0351 (10)0.0404 (8)−0.0013 (7)−0.0033 (7)0.0026 (7)
C120.0332 (8)0.0476 (11)0.0506 (10)0.0030 (8)−0.0019 (7)0.0007 (8)
C130.0387 (9)0.0341 (10)0.0431 (9)−0.0050 (7)−0.0058 (7)0.0045 (7)
C140.0502 (11)0.0557 (13)0.0486 (10)−0.0079 (9)−0.0138 (8)−0.0009 (9)
C150.0689 (13)0.0558 (14)0.0431 (10)−0.0075 (10)−0.0046 (9)−0.0087 (9)
C160.0559 (11)0.0509 (13)0.0507 (10)0.0038 (9)0.0047 (8)−0.0040 (9)
C170.0401 (9)0.0415 (11)0.0473 (9)0.0018 (7)−0.0013 (7)0.0025 (8)
C180.0360 (8)0.0295 (9)0.0386 (8)−0.0029 (7)−0.0036 (6)0.0060 (7)
Geometric parameters (Å, °) top
O1—C111.3622 (18)C7—H70.9300
O1—C11.4073 (18)C8—C91.391 (3)
N1—C121.297 (2)C8—H80.9300
N1—C131.377 (2)C9—C101.363 (3)
N2—C111.2928 (19)C9—H90.9300
N2—C181.3778 (19)C10—H100.9300
C1—C61.352 (2)C11—C121.421 (2)
C1—C21.398 (2)C12—H120.9300
C2—C31.359 (2)C13—C141.405 (2)
C2—H20.9300C13—C181.411 (2)
C3—C41.410 (2)C14—C151.360 (3)
C3—H30.9300C14—H140.9300
C4—C51.415 (2)C15—C161.399 (2)
C4—C71.415 (2)C15—H150.9300
C5—C101.410 (2)C16—C171.361 (2)
C5—C61.414 (2)C16—H160.9300
C6—H60.9300C17—C181.401 (2)
C7—C81.357 (2)C17—H170.9300
C11—O1—C1118.73 (12)C8—C9—H9119.8
C12—N1—C13116.62 (13)C9—C10—C5120.83 (19)
C11—N2—C18115.58 (13)C9—C10—H10119.6
C6—C1—C2122.30 (15)C5—C10—H10119.6
C6—C1—O1117.50 (15)N2—C11—O1121.55 (13)
C2—C1—O1119.95 (14)N2—C11—C12124.14 (15)
C3—C2—C1118.92 (15)O1—C11—C12114.31 (14)
C3—C2—H2120.5N1—C12—C11121.72 (15)
C1—C2—H2120.5N1—C12—H12119.1
C2—C3—C4121.39 (16)C11—C12—H12119.1
C2—C3—H3119.3N1—C13—C14119.82 (15)
C4—C3—H3119.3N1—C13—C18121.02 (14)
C3—C4—C5118.72 (14)C14—C13—C18119.14 (15)
C3—C4—C7122.55 (16)C15—C14—C13120.36 (16)
C5—C4—C7118.72 (15)C15—C14—H14119.8
C10—C5—C4118.70 (15)C13—C14—H14119.8
C10—C5—C6122.33 (16)C14—C15—C16120.19 (16)
C4—C5—C6118.97 (14)C14—C15—H15119.9
C1—C6—C5119.65 (15)C16—C15—H15119.9
C1—C6—H6120.2C17—C16—C15120.98 (17)
C5—C6—H6120.2C17—C16—H16119.5
C8—C7—C4120.72 (17)C15—C16—H16119.5
C8—C7—H7119.6C16—C17—C18119.89 (16)
C4—C7—H7119.6C16—C17—H17120.1
C7—C8—C9120.65 (17)C18—C17—H17120.1
C7—C8—H8119.7N2—C18—C17119.67 (14)
C9—C8—H8119.7N2—C18—C13120.91 (14)
C10—C9—C8120.38 (18)C17—C18—C13119.43 (14)
C10—C9—H9119.8
C11—O1—C1—C6−119.60 (16)C18—N2—C11—O1178.93 (14)
C11—O1—C1—C265.9 (2)C18—N2—C11—C12−0.3 (2)
C6—C1—C2—C32.0 (3)C1—O1—C11—N21.5 (2)
O1—C1—C2—C3176.20 (15)C1—O1—C11—C12−179.20 (15)
C1—C2—C3—C4−1.1 (3)C13—N1—C12—C110.3 (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—C14178.37 (16)
C7—C4—C5—C100.8 (2)C12—N1—C13—C180.1 (2)
C3—C4—C5—C61.7 (2)N1—C13—C14—C15−178.25 (17)
C7—C4—C5—C6−179.25 (15)C18—C13—C14—C150.0 (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—C1179.15 (16)C15—C16—C17—C181.1 (3)
C4—C5—C6—C1−0.8 (2)C11—N2—C18—C17−179.07 (14)
C3—C4—C7—C8178.35 (17)C11—N2—C18—C130.8 (2)
C5—C4—C7—C8−0.7 (3)C16—C17—C18—N2178.38 (15)
C4—C7—C8—C9−0.2 (3)C16—C17—C18—C13−1.5 (2)
C7—C8—C9—C101.0 (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—C90.0 (3)N1—C13—C18—C17179.13 (15)
C6—C5—C10—C9−179.97 (18)C14—C13—C18—C170.9 (2)
Acknowledgements top

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

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Hassan, N. D., Tajuddin, H. A., Abdullah, Z. & Ng, S. W. (2009). Acta Cryst. E65. Submitted. [TK2386]

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2009). publCIF. In preparation.