1-Naphthyl quinoxalin-2-yl ether

organic compounds Acta Crystallographica Section E b = 18.5123 (6) Å c = 7.7947 (3) Å V = 2637.2 (2) Å3 Z=8 Structure Reports Online Mo K radiation  = 0.09 mm 1 T = 118 K 0.12  0.04  0.02 mm ISSN 1600-5368 Data collection 1-Naphthyl quinoxalin-2-yl ether Noor Doha Hassan, Hairul Anuar Tajuddin, Zanariah Abdullah and Seik Weng Ng* Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia Correspondence e-mail: [email protected] Received 2 March 2009; accepted 4 March 2009 Key indicators: single-crystal X-ray study; T = 118 K; mean (C–C) = 0.004 Å; R factor = 0.038; wR factor = 0.087; data-to-parameter ratio = 8.6. 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 2phenyl ether, see: Abdullah & Ng (2008); Hassan et al. (2008). Bruker SMART APEX diffractometer Absorption correction: none 12370 measured reflections 1626 independent reflections 1316 reflections with I > 2(I) Rint = 0.071 Refinement R[F 2 > 2(F 2)] = 0.038 wR(F 2) = 0.087 S = 1.02 1626 reflections 190 parameters 1 restraint H-atom parameters constrained
max = 0.19 e Å 3
min = 0.24 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: XSEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009). We thank the University of Malaya for supporting this study (FS358/2008 A). Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2386). References Experimental Crystal data C18H12N2O Mr = 272.30 Acta Cryst. (2009). E65, o731 Orthorhombic, Aba2 a = 18.2758 (6) Å 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. doi:10.1107/S1600536809007867 Hassan et al. o731 supporting information supporting information Acta Cryst. (2009). E65, o731 [doi:10.1107/S1600536809007867] 1-Naphthyl quinoxalin-2-yl ether Noor Doha Hassan, Hairul Anuar Tajuddin, Zanariah Abdullah and Seik Weng Ng S1. 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. S2. 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. Figure 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 Crystal data C18H12N2O Mr = 272.30 Orthorhombic, Aba2 Hall symbol: A 2 -2ac Acta Cryst. (2009). E65, o731 a = 18.2758 (6) Å b = 18.5123 (6) Å c = 7.7947 (3) Å V = 2637.2 (2) Å3 sup-1 supporting information Z=8 F(000) = 1136 Dx = 1.372 Mg m−3 Mo Kα radiation, λ = 0.71073 Å Cell parameters from 1495 reflections θ = 2.2–21.2° µ = 0.09 mm−1 T = 118 K Prism, colorless 0.12 × 0.04 × 0.02 mm Data collection 1316 reflections with I > 2σ(I) Rint = 0.071 θmax = 27.5°, θmin = 2.2° h = −22→23 k = −24→23 l = −10→10 Bruker SMART APEX diffractometer Radiation source: fine-focus sealed tube Graphite monochromator ω scans 12370 measured reflections 1626 independent reflections Refinement Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.038 wR(F2) = 0.087 S = 1.02 1626 reflections 190 parameters 1 restraint Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ2(Fo2) + (0.046P)2 + 0.5804P] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max = 0.001 Δρmax = 0.19 e Å−3 Δρmin = −0.24 e Å−3 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) O1 N1 N2 C1 C2 H2 C3 H3 C4 H4 C5 C6 H6 C7 H7 C8 x y z Uiso*/Ueq 0.19391 (9) 0.15328 (11) 0.30285 (11) 0.12235 (13) 0.07744 (14) 0.0930 0.00734 (14) −0.0246 −0.01480 (14) −0.0619 0.03121 (13) 0.00887 (15) −0.0381 0.05358 (16) 0.0375 0.12373 (16) 0.24366 (9) 0.34927 (11) 0.38838 (11) 0.21546 (12) 0.22066 (13) 0.2454 0.18873 (13) 0.1922 0.15306 (13) 0.1314 0.14761 (12) 0.11230 (14) 0.0903 0.10925 (15) 0.0857 0.14110 (15) 0.5000 (2) 0.3713 (3) 0.3387 (3) 0.4887 (4) 0.6269 (4) 0.7273 0.6196 (3) 0.7155 0.4762 (3) 0.4737 0.3301 (3) 0.1784 (4) 0.1737 0.0388 (4) −0.0627 0.0448 (4) 0.0217 (4) 0.0192 (5) 0.0218 (5) 0.0192 (5) 0.0222 (6) 0.027* 0.0234 (6) 0.028* 0.0231 (6) 0.028* 0.0198 (5) 0.0269 (6) 0.032* 0.0301 (7) 0.036* 0.0278 (6) Acta Cryst. (2009). E65, o731 sup-2 supporting information H8 C9 H9 C10 C11 C12 H12 C13 C14 H14 C15 H15 C16 H16 C17 H17 C18 0.1546 0.14764 (14) 0.1952 0.10190 (13) 0.20655 (14) 0.28187 (14) 0.3178 0.24804 (15) 0.26686 (14) 0.3168 0.21262 (15) 0.2253 0.13869 (15) 0.1017 0.11934 (14) 0.0691 0.17350 (13) 0.1388 0.17502 (13) 0.1957 0.17973 (13) 0.30943 (13) 0.32836 (13) 0.2964 0.43279 (12) 0.49812 (13) 0.5114 0.54275 (14) 0.5866 0.52397 (13) 0.5552 0.46108 (13) 0.4494 0.41378 (13) −0.0531 0.1890 (4) 0.1917 0.3355 (3) 0.4253 (3) 0.4113 (3) 0.4560 0.2773 (3) 0.1965 (4) 0.1841 0.1356 (4) 0.0798 0.1552 (4) 0.1123 0.2357 (3) 0.2501 0.2971 (3) 0.033* 0.0219 (6) 0.026* 0.0180 (5) 0.0189 (5) 0.0213 (6) 0.026* 0.0190 (5) 0.0232 (6) 0.028* 0.0247 (6) 0.030* 0.0231 (6) 0.028* 0.0212 (6) 0.025* 0.0190 (5) Atomic displacement parameters (Å2) O1 N1 N2 C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 U11 U22 U33 U12 U13 U23 0.0185 (9) 0.0177 (11) 0.0202 (11) 0.0154 (13) 0.0246 (14) 0.0228 (14) 0.0164 (13) 0.0179 (13) 0.0244 (14) 0.0321 (16) 0.0325 (15) 0.0206 (13) 0.0184 (12) 0.0225 (14) 0.0193 (14) 0.0191 (12) 0.0226 (14) 0.0312 (15) 0.0243 (14) 0.0192 (13) 0.0205 (13) 0.0192 (9) 0.0189 (10) 0.0228 (11) 0.0156 (11) 0.0183 (12) 0.0215 (13) 0.0212 (12) 0.0159 (12) 0.0236 (13) 0.0316 (15) 0.0312 (15) 0.0194 (12) 0.0152 (11) 0.0169 (12) 0.0229 (13) 0.0193 (11) 0.0226 (12) 0.0203 (12) 0.0199 (12) 0.0199 (12) 0.0160 (11) 0.0275 (10) 0.0211 (12) 0.0223 (11) 0.0266 (14) 0.0237 (14) 0.0259 (15) 0.0316 (16) 0.0255 (14) 0.0326 (16) 0.0266 (16) 0.0198 (14) 0.0257 (14) 0.0205 (13) 0.0172 (12) 0.0217 (13) 0.0184 (13) 0.0243 (14) 0.0225 (14) 0.0252 (14) 0.0245 (14) 0.0204 (13) −0.0015 (7) −0.0005 (8) −0.0011 (8) 0.0005 (9) 0.0038 (10) 0.0046 (10) 0.0026 (9) 0.0015 (10) −0.0003 (11) 0.0045 (12) 0.0087 (12) 0.0031 (10) 0.0019 (9) −0.0021 (10) 0.0016 (10) 0.0000 (10) −0.0037 (10) −0.0016 (11) 0.0032 (10) −0.0004 (10) −0.0010 (10) −0.0032 (8) −0.0005 (8) −0.0006 (10) −0.0035 (12) −0.0013 (12) 0.0077 (12) 0.0011 (12) −0.0038 (11) −0.0065 (13) −0.0094 (13) 0.0021 (12) 0.0009 (11) −0.0007 (11) −0.0020 (11) −0.0012 (11) −0.0003 (10) 0.0031 (12) 0.0019 (12) −0.0034 (12) −0.0005 (11) 0.0000 (11) 0.0043 (8) 0.0002 (9) −0.0001 (10) 0.0063 (11) 0.0002 (11) 0.0030 (12) 0.0054 (12) 0.0057 (11) −0.0009 (13) −0.0040 (13) 0.0017 (12) 0.0065 (12) 0.0045 (10) −0.0011 (10) −0.0018 (11) −0.0023 (10) −0.0002 (12) 0.0017 (11) −0.0006 (11) −0.0023 (11) −0.0043 (11) Geometric parameters (Å, º) O1—C11 O1—C1 N1—C11 Acta Cryst. (2009). E65, o731 1.369 (3) 1.411 (3) 1.292 (3) C7—C8 C7—H7 C8—C9 1.412 (4) 0.9500 1.360 (4) sup-3 supporting information N1—C18 N2—C12 N2—C13 C1—C2 C1—C10 C2—C3 C2—H2 C3—C4 C3—H3 C4—C5 C4—H4 C5—C6 C5—C10 C6—C7 C6—H6 1.378 (3) 1.304 (3) 1.382 (3) 1.358 (4) 1.415 (3) 1.412 (4) 0.9500 1.360 (4) 0.9500 1.419 (4) 0.9500 1.411 (4) 1.423 (3) 1.362 (4) 0.9500 C8—H8 C9—C10 C9—H9 C11—C12 C12—H12 C13—C14 C13—C18 C14—C15 C14—H14 C15—C16 C15—H15 C16—C17 C16—H16 C17—C18 C17—H17 0.9500 1.418 (3) 0.9500 1.425 (3) 0.9500 1.406 (3) 1.415 (4) 1.375 (4) 0.9500 1.404 (4) 0.9500 1.369 (4) 0.9500 1.405 (3) 0.9500 C11—O1—C1 C11—N1—C18 C12—N2—C13 C2—C1—O1 C2—C1—C10 O1—C1—C10 C1—C2—C3 C1—C2—H2 C3—C2—H2 C4—C3—C2 C4—C3—H3 C2—C3—H3 C3—C4—C5 C3—C4—H4 C5—C4—H4 C6—C5—C4 C6—C5—C10 C4—C5—C10 C7—C6—C5 C7—C6—H6 C5—C6—H6 C6—C7—C8 C6—C7—H7 C8—C7—H7 C9—C8—C7 C9—C8—H8 C7—C8—H8 C8—C9—C10 C8—C9—H9 117.31 (18) 115.4 (2) 116.4 (2) 119.0 (2) 122.9 (2) 118.1 (2) 119.1 (2) 120.5 120.5 120.4 (2) 119.8 119.8 121.2 (2) 119.4 119.4 122.3 (2) 118.8 (2) 119.0 (2) 121.0 (2) 119.5 119.5 120.0 (3) 120.0 120.0 120.8 (3) 119.6 119.6 120.3 (2) 119.8 C10—C9—H9 C1—C10—C9 C1—C10—C5 C9—C10—C5 N1—C11—O1 N1—C11—C12 O1—C11—C12 N2—C12—C11 N2—C12—H12 C11—C12—H12 N2—C13—C14 N2—C13—C18 C14—C13—C18 C15—C14—C13 C15—C14—H14 C13—C14—H14 C14—C15—C16 C14—C15—H15 C16—C15—H15 C17—C16—C15 C17—C16—H16 C15—C16—H16 C16—C17—C18 C16—C17—H17 C18—C17—H17 N1—C18—C17 N1—C18—C13 C17—C18—C13 119.8 123.5 (2) 117.4 (2) 119.1 (2) 121.3 (2) 124.2 (2) 114.5 (2) 121.8 (2) 119.1 119.1 119.3 (2) 120.8 (2) 119.9 (2) 119.7 (2) 120.2 120.2 120.5 (2) 119.7 119.7 120.6 (2) 119.7 119.7 120.3 (2) 119.9 119.9 119.6 (2) 121.3 (2) 119.1 (2) C11—O1—C1—C2 C11—O1—C1—C10 −101.4 (3) 81.6 (3) C18—N1—C11—O1 C18—N1—C11—C12 −179.3 (2) −0.3 (4) Acta Cryst. (2009). E65, o731 sup-4 supporting information O1—C1—C2—C3 C10—C1—C2—C3 C1—C2—C3—C4 C2—C3—C4—C5 C3—C4—C5—C6 C3—C4—C5—C10 C4—C5—C6—C7 C10—C5—C6—C7 C5—C6—C7—C8 C6—C7—C8—C9 C7—C8—C9—C10 C2—C1—C10—C9 O1—C1—C10—C9 C2—C1—C10—C5 O1—C1—C10—C5 C8—C9—C10—C1 C8—C9—C10—C5 C6—C5—C10—C1 C4—C5—C10—C1 C6—C5—C10—C9 C4—C5—C10—C9 Acta Cryst. (2009). E65, o731 −176.3 (2) 0.5 (3) 0.2 (3) −0.7 (4) −178.6 (2) 0.5 (3) 178.6 (2) −0.5 (4) 0.6 (4) 0.1 (4) −0.8 (4) 178.8 (2) −4.4 (3) −0.7 (3) 176.1 (2) −178.6 (2) 0.9 (4) 179.3 (2) 0.2 (3) −0.2 (3) −179.3 (2) C1—O1—C11—N1 C1—O1—C11—C12 C13—N2—C12—C11 N1—C11—C12—N2 O1—C11—C12—N2 C12—N2—C13—C14 C12—N2—C13—C18 N2—C13—C14—C15 C18—C13—C14—C15 C13—C14—C15—C16 C14—C15—C16—C17 C15—C16—C17—C18 C11—N1—C18—C17 C11—N1—C18—C13 C16—C17—C18—N1 C16—C17—C18—C13 N2—C13—C18—N1 C14—C13—C18—N1 N2—C13—C18—C17 C14—C13—C18—C17 10.9 (3) −168.2 (2) 0.4 (4) −1.0 (4) 178.1 (2) −179.6 (2) 1.4 (4) −179.7 (2) −0.7 (4) 0.7 (4) 0.2 (4) −1.2 (4) −179.5 (2) 2.1 (3) −177.3 (2) 1.2 (4) −2.8 (4) 178.2 (2) 178.8 (2) −0.3 (4) sup-5