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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o732.
Published online 2009 March 11. doi:  10.1107/S1600536809007855
PMCID: PMC2968896

2-Naphthyl quinoxalin-2-yl ether

Abstract

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 [triangle]).

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Object name is e-65-0o732-scheme1.jpg

Experimental

Crystal data

  • C18H12N2O
  • M r = 272.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o732-efi1.jpg
  • 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[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.127
  • S = 1.04
  • 3094 reflections
  • 190 parameters
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

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

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

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

Acknowledgments

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

supplementary crystallographic information

Experimental

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

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).

Figures

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.

Crystal data

C18H12N2OF(000) = 568
Mr = 272.30Dx = 1.332 Mg m3
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 mm1
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

Bruker SMART APEX diffractometer1950 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

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 = 1.04w = 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 Å3
0 restraintsΔρmin = −0.16 e Å3

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

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)

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, °)

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)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2387).

References

  • 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, o731. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography