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Acta Cryst. (2009). E65, o731    [ doi:10.1107/S1600536809007867 ]

1-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 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 top

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

Experimental top

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 top

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.

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 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
1-Naphthyl quinoxalin-2-yl ether top
Crystal data top
C18H12N2OF(000) = 1136
Mr = 272.30Dx = 1.372 Mg m−3
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 mm−1
c = 7.7947 (3) ÅT = 118 K
V = 2637.2 (2) Å3Prism, colorless
Z = 80.12 × 0.04 × 0.02 mm
Data collection top
Bruker SMART APEX
diffractometer		1316 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 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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-atom parameters constrained
S = 1.02 w = 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 Å−3
1 restraintΔρmin = −0.24 e Å−3
Crystal data top
C18H12N2OV = 2637.2 (2) Å3
Mr = 272.30Z = 8
Orthorhombic, Aba2Mo Kα radiation
a = 18.2758 (6) ŵ = 0.09 mm−1
b = 18.5123 (6) ÅT = 118 K
c = 7.7947 (3) Å0.12 × 0.04 × 0.02 mm
Data collection top
Bruker SMART APEX
diffractometer		1316 reflections with I > 2σ(I)
12370 measured reflectionsRint = 0.071
1626 independent reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.087Δρmax = 0.19 e Å−3
S = 1.02Δρmin = −0.24 e Å−3
1626 reflectionsAbsolute structure: ?
190 parametersFlack parameter: ?
1 restraintRogers parameter: ?
Special details top

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) top
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) top
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, °) top
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)
Acknowledgements top

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

references
References top

Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2165.

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.

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

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