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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o731.
Published online 2009 March 11. doi:  10.1107/S1600536809007867
PMCID: PMC2968882

1-Naphthyl quinoxalin-2-yl ether

Abstract

In the crystal structure of the title compound, C18H12N2O, the dihedral angle between the two fused-ring systems is 84.3 (1) °; the C—O—C angle at the ether O atom is 117.31 (18)°.

Related literature

For the crystal structure of the two forms of quinoxalinyl 2-phenyl ether, see: Abdullah & Ng (2008 [triangle]); Hassan et al. (2008 [triangle]).

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Object name is e-65-0o731-scheme1.jpg

Experimental

Crystal data

  • C18H12N2O
  • M r = 272.30
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o731-efi1.jpg
  • a = 18.2758 (6) Å
  • b = 18.5123 (6) Å
  • c = 7.7947 (3) Å
  • V = 2637.2 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 118 K
  • 0.12 × 0.04 × 0.02 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 12370 measured reflections
  • 1626 independent reflections
  • 1316 reflections with I > 2σ(I)
  • R int = 0.071

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.087
  • S = 1.02
  • 1626 reflections
  • 190 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.24 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/S1600536809007867/tk2386sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007867/tk2386Isup2.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

1-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 a chloroform/ether mixture.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 Å) and were included in the refinement in the riding model approximation, with U(H) = 1.2Ueq(C). In the absence of significant anomalous scattering effects, Friedel pairs were averaged in the final refinement.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the molecule of C18H12N2O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C18H12N2OF(000) = 1136
Mr = 272.30Dx = 1.372 Mg m3
Orthorhombic, Aba2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: A 2 -2acCell parameters from 1495 reflections
a = 18.2758 (6) Åθ = 2.2–21.2°
b = 18.5123 (6) ŵ = 0.09 mm1
c = 7.7947 (3) ÅT = 118 K
V = 2637.2 (2) Å3Prism, colorless
Z = 80.12 × 0.04 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer1316 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.071
graphiteθmax = 27.5°, θmin = 2.2°
ω scansh = −22→23
12370 measured reflectionsk = −24→23
1626 independent reflectionsl = −10→10

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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.046P)2 + 0.5804P] where P = (Fo2 + 2Fc2)/3
1626 reflections(Δ/σ)max = 0.001
190 parametersΔρmax = 0.19 e Å3
1 restraintΔρmin = −0.24 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

xyzUiso*/Ueq
O10.19391 (9)0.24366 (9)0.5000 (2)0.0217 (4)
N10.15328 (11)0.34927 (11)0.3713 (3)0.0192 (5)
N20.30285 (11)0.38838 (11)0.3387 (3)0.0218 (5)
C10.12235 (13)0.21546 (12)0.4887 (4)0.0192 (5)
C20.07744 (14)0.22066 (13)0.6269 (4)0.0222 (6)
H20.09300.24540.72730.027*
C30.00734 (14)0.18873 (13)0.6196 (3)0.0234 (6)
H3−0.02460.19220.71550.028*
C4−0.01480 (14)0.15306 (13)0.4762 (3)0.0231 (6)
H4−0.06190.13140.47370.028*
C50.03121 (13)0.14761 (12)0.3301 (3)0.0198 (5)
C60.00887 (15)0.11230 (14)0.1784 (4)0.0269 (6)
H6−0.03810.09030.17370.032*
C70.05358 (16)0.10925 (15)0.0388 (4)0.0301 (7)
H70.03750.0857−0.06270.036*
C80.12373 (16)0.14110 (15)0.0448 (4)0.0278 (6)
H80.15460.1388−0.05310.033*
C90.14764 (14)0.17502 (13)0.1890 (4)0.0219 (6)
H90.19520.19570.19170.026*
C100.10190 (13)0.17973 (13)0.3355 (3)0.0180 (5)
C110.20655 (14)0.30943 (13)0.4253 (3)0.0189 (5)
C120.28187 (14)0.32836 (13)0.4113 (3)0.0213 (6)
H120.31780.29640.45600.026*
C130.24804 (15)0.43279 (12)0.2773 (3)0.0190 (5)
C140.26686 (14)0.49812 (13)0.1965 (4)0.0232 (6)
H140.31680.51140.18410.028*
C150.21262 (15)0.54275 (14)0.1356 (4)0.0247 (6)
H150.22530.58660.07980.030*
C160.13869 (15)0.52397 (13)0.1552 (4)0.0231 (6)
H160.10170.55520.11230.028*
C170.11934 (14)0.46108 (13)0.2357 (3)0.0212 (6)
H170.06910.44940.25010.025*
C180.17350 (13)0.41378 (13)0.2971 (3)0.0190 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0185 (9)0.0192 (9)0.0275 (10)−0.0015 (7)−0.0032 (8)0.0043 (8)
N10.0177 (11)0.0189 (10)0.0211 (12)−0.0005 (8)−0.0005 (8)0.0002 (9)
N20.0202 (11)0.0228 (11)0.0223 (11)−0.0011 (8)−0.0006 (10)−0.0001 (10)
C10.0154 (13)0.0156 (11)0.0266 (14)0.0005 (9)−0.0035 (12)0.0063 (11)
C20.0246 (14)0.0183 (12)0.0237 (14)0.0038 (10)−0.0013 (12)0.0002 (11)
C30.0228 (14)0.0215 (13)0.0259 (15)0.0046 (10)0.0077 (12)0.0030 (12)
C40.0164 (13)0.0212 (12)0.0316 (16)0.0026 (9)0.0011 (12)0.0054 (12)
C50.0179 (13)0.0159 (12)0.0255 (14)0.0015 (10)−0.0038 (11)0.0057 (11)
C60.0244 (14)0.0236 (13)0.0326 (16)−0.0003 (11)−0.0065 (13)−0.0009 (13)
C70.0321 (16)0.0316 (15)0.0266 (16)0.0045 (12)−0.0094 (13)−0.0040 (13)
C80.0325 (15)0.0312 (15)0.0198 (14)0.0087 (12)0.0021 (12)0.0017 (12)
C90.0206 (13)0.0194 (12)0.0257 (14)0.0031 (10)0.0009 (11)0.0065 (12)
C100.0184 (12)0.0152 (11)0.0205 (13)0.0019 (9)−0.0007 (11)0.0045 (10)
C110.0225 (14)0.0169 (12)0.0172 (12)−0.0021 (10)−0.0020 (11)−0.0011 (10)
C120.0193 (14)0.0229 (13)0.0217 (13)0.0016 (10)−0.0012 (11)−0.0018 (11)
C130.0191 (12)0.0193 (11)0.0184 (13)0.0000 (10)−0.0003 (10)−0.0023 (10)
C140.0226 (14)0.0226 (12)0.0243 (14)−0.0037 (10)0.0031 (12)−0.0002 (12)
C150.0312 (15)0.0203 (12)0.0225 (14)−0.0016 (11)0.0019 (12)0.0017 (11)
C160.0243 (14)0.0199 (12)0.0252 (14)0.0032 (10)−0.0034 (12)−0.0006 (11)
C170.0192 (13)0.0199 (12)0.0245 (14)−0.0004 (10)−0.0005 (11)−0.0023 (11)
C180.0205 (13)0.0160 (11)0.0204 (13)−0.0010 (10)0.0000 (11)−0.0043 (11)

Geometric parameters (Å, °)

O1—C111.369 (3)C7—C81.412 (4)
O1—C11.411 (3)C7—H70.9500
N1—C111.292 (3)C8—C91.360 (4)
N1—C181.378 (3)C8—H80.9500
N2—C121.304 (3)C9—C101.418 (3)
N2—C131.382 (3)C9—H90.9500
C1—C21.358 (4)C11—C121.425 (3)
C1—C101.415 (3)C12—H120.9500
C2—C31.412 (4)C13—C141.406 (3)
C2—H20.9500C13—C181.415 (4)
C3—C41.360 (4)C14—C151.375 (4)
C3—H30.9500C14—H140.9500
C4—C51.419 (4)C15—C161.404 (4)
C4—H40.9500C15—H150.9500
C5—C61.411 (4)C16—C171.369 (4)
C5—C101.423 (3)C16—H160.9500
C6—C71.362 (4)C17—C181.405 (3)
C6—H60.9500C17—H170.9500
C11—O1—C1117.31 (18)C10—C9—H9119.8
C11—N1—C18115.4 (2)C1—C10—C9123.5 (2)
C12—N2—C13116.4 (2)C1—C10—C5117.4 (2)
C2—C1—O1119.0 (2)C9—C10—C5119.1 (2)
C2—C1—C10122.9 (2)N1—C11—O1121.3 (2)
O1—C1—C10118.1 (2)N1—C11—C12124.2 (2)
C1—C2—C3119.1 (2)O1—C11—C12114.5 (2)
C1—C2—H2120.5N2—C12—C11121.8 (2)
C3—C2—H2120.5N2—C12—H12119.1
C4—C3—C2120.4 (2)C11—C12—H12119.1
C4—C3—H3119.8N2—C13—C14119.3 (2)
C2—C3—H3119.8N2—C13—C18120.8 (2)
C3—C4—C5121.2 (2)C14—C13—C18119.9 (2)
C3—C4—H4119.4C15—C14—C13119.7 (2)
C5—C4—H4119.4C15—C14—H14120.2
C6—C5—C4122.3 (2)C13—C14—H14120.2
C6—C5—C10118.8 (2)C14—C15—C16120.5 (2)
C4—C5—C10119.0 (2)C14—C15—H15119.7
C7—C6—C5121.0 (2)C16—C15—H15119.7
C7—C6—H6119.5C17—C16—C15120.6 (2)
C5—C6—H6119.5C17—C16—H16119.7
C6—C7—C8120.0 (3)C15—C16—H16119.7
C6—C7—H7120.0C16—C17—C18120.3 (2)
C8—C7—H7120.0C16—C17—H17119.9
C9—C8—C7120.8 (3)C18—C17—H17119.9
C9—C8—H8119.6N1—C18—C17119.6 (2)
C7—C8—H8119.6N1—C18—C13121.3 (2)
C8—C9—C10120.3 (2)C17—C18—C13119.1 (2)
C8—C9—H9119.8
C11—O1—C1—C2−101.4 (3)C18—N1—C11—O1−179.3 (2)
C11—O1—C1—C1081.6 (3)C18—N1—C11—C12−0.3 (4)
O1—C1—C2—C3−176.3 (2)C1—O1—C11—N110.9 (3)
C10—C1—C2—C30.5 (3)C1—O1—C11—C12−168.2 (2)
C1—C2—C3—C40.2 (3)C13—N2—C12—C110.4 (4)
C2—C3—C4—C5−0.7 (4)N1—C11—C12—N2−1.0 (4)
C3—C4—C5—C6−178.6 (2)O1—C11—C12—N2178.1 (2)
C3—C4—C5—C100.5 (3)C12—N2—C13—C14−179.6 (2)
C4—C5—C6—C7178.6 (2)C12—N2—C13—C181.4 (4)
C10—C5—C6—C7−0.5 (4)N2—C13—C14—C15−179.7 (2)
C5—C6—C7—C80.6 (4)C18—C13—C14—C15−0.7 (4)
C6—C7—C8—C90.1 (4)C13—C14—C15—C160.7 (4)
C7—C8—C9—C10−0.8 (4)C14—C15—C16—C170.2 (4)
C2—C1—C10—C9178.8 (2)C15—C16—C17—C18−1.2 (4)
O1—C1—C10—C9−4.4 (3)C11—N1—C18—C17−179.5 (2)
C2—C1—C10—C5−0.7 (3)C11—N1—C18—C132.1 (3)
O1—C1—C10—C5176.1 (2)C16—C17—C18—N1−177.3 (2)
C8—C9—C10—C1−178.6 (2)C16—C17—C18—C131.2 (4)
C8—C9—C10—C50.9 (4)N2—C13—C18—N1−2.8 (4)
C6—C5—C10—C1179.3 (2)C14—C13—C18—N1178.2 (2)
C4—C5—C10—C10.2 (3)N2—C13—C18—C17178.8 (2)
C6—C5—C10—C9−0.2 (3)C14—C13—C18—C17−0.3 (4)
C4—C5—C10—C9−179.3 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2386).

References

  • Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2165. [PMC free article] [PubMed]
  • 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. (2008). Acta Cryst. E64, o1820. [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