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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1821. | PMCID: PMC2960597 |
Quinoxalin-2-yl o-tolyl ether Nor Duha Hassan,a Hairul Anuar Tajuddin,a Zanariah Abdullah,a and Seik Weng Nga* aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia Received August 12, 2008; Accepted August 19, 2008. This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. The dihedral angle between the two aromatic ring systems in the title compound, C15H12N2O, is 85.9 (1)°; The angle at the O atom is widened to 118.2 (2)°. The quinoxalinyloxy part of the molecule lies on a mirror plane and the tolyl group is disordered over two positions about the mirror plane. The title compound exhibits fluorescence; see: Abdullah (2005 ![[triangle]](/corehtml/pmc/pmcents/rtrif.gif) ); Kawai et al. (2001 ); Mohd Salleh et al. (2007 ). Click on image to enlarge  Crystal data
- C15H12N2O
-
M
r = 236.27
- Monoclinic,
-
a = 7.874 (2) Å
-
b = 7.413 (1) Å
-
c = 10.596 (2) Å
- β = 108.332 (3)°
-
V = 587.1 (2) Å3
-
Z = 2
- Mo Kα radiation
- μ = 0.09 mm−1
-
T = 100 (2) K
- 0.20 × 0.20 × 0.08 mm
Data collection
- Bruker SMART APEX diffractometer
- Absorption correction: none
- 3392 measured reflections
- 1443 independent reflections
- 1032 reflections with I > 2σ(I)
-
R
int = 0.026
Refinement
-
R[F
2 > 2σ(F
2)] = 0.065
-
wR(F
2) = 0.183
-
S = 1.03
- 1443 reflections
- 119 parameters
- H-atom parameters constrained
- Δρmax = 0.24 e Å−3
- Δρmin = −0.31 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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2008 ). We thank the University of Malaya for supporting this study (grant No. F2358/2008 A). supplementary crystallographic
information
Experimental o-Cresol (0.54 g, 5 mmol) was dissolved in a small volume of water
containing potassium hydroxide (0.20 g, 5 mmol). The mixture was heated to
remove the water to give a brown compound. The compound and
2-chloroquinoxaline (0.82, g, 5 mmol) were heated in THF (15 ml) for 8 h. The
mixture was in 1 N sodium hydroxide; the aqueous solution was extracted with
dichloromethane. The organic phase was dried over sodium sulfate. Evaporation
of the solvent gave a yellow product, which was was washed with chloroform to
remove impurities. Crystals were obtained upon recrystallization from an ethyl
acetate/hexane mixture.
Refinement The tolyl group is disordered about a mirror plane; the phenylene ring was
refined as a rigid hexagon. The seven carbon atoms were allowed to refine off
the symmetry element; the atoms were all given 0.5 site occupancy. H-atoms were placed in calculated positions (C—H 0.95–0.98 Å) and were included in the refinement in the riding model approximation,
with U(H) fixed at 1.2–1.5U(C). Crystal data | C15H12N2O | F000 = 248 | | Mr = 236.27 | Dx = 1.337 Mg m−3 | | Monoclinic, P21/m | Mo Kα radiation λ = 0.71073 Å | | Hall symbol: -P 2yb | Cell parameters from 756 reflections | | a = 7.874 (2) Å | θ = 2.7–24.6º | | b = 7.413 (1) Å | µ = 0.09 mm−1 | | c = 10.596 (2) Å | T = 100 (2) K | | β = 108.332 (3)º | Block, colorless | | V = 587.1 (2) Å3 | 0.20 × 0.20 × 0.08 mm | | Z = 2 | |
Data collection | Bruker SMART APEX diffractometer | 1032 reflections with I > 2σ(I) | | Radiation source: fine-focus sealed tube | Rint = 0.027 | | Monochromator: graphite | θmax = 27.5º | | T = 100(2) K | θmin = 2.0º | | ω scans | h = −10→8 | | Absorption correction: None | k = −9→8 | | 3392 measured reflections | l = −12→13 | | 1443 independent reflections | |
Refinement | Refinement on F2 | Secondary atom site location: difference Fourier map | | Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites | | R[F2 > 2σ(F2)] = 0.065 | H-atom parameters constrained | | wR(F2) = 0.183 | w = 1/[σ2(Fo2) + (0.0776P)2 + 0.4106P] where P = (Fo2 + 2Fc2)/3 | | S = 1.03 | (Δ/σ)max = 0.001 | | 1443 reflections | Δρmax = 0.24 e Å−3 | | 119 parameters | Δρmin = −0.31 e Å−3 | | Primary atom site location: structure-invariant direct methods | Extinction correction: none |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) | x | y | z | Uiso*/Ueq | Occ. (<1) | | O1 | 0.1778 (2) | 0.2500 | 0.64890 (18) | 0.0405 (6) | | | N1 | 0.4752 (3) | 0.2500 | 0.7791 (2) | 0.0552 (9) | | | N2 | 0.3518 (3) | 0.2500 | 0.9997 (2) | 0.0479 (8) | | | C1 | 0.2266 (3) | 0.1943 (3) | 0.5368 (2) | 0.0256 (8) | 0.50 | | C2 | 0.2256 (5) | 0.0171 (3) | 0.4936 (3) | 0.047 (2) | 0.50 | | H2 | 0.2002 | −0.0787 | 0.5445 | 0.056* | 0.50 | | C3 | 0.2619 (5) | −0.0199 (3) | 0.3761 (3) | 0.0473 (11) | 0.50 | | H3 | 0.2612 | −0.1410 | 0.3466 | 0.057* | 0.50 | | C4 | 0.2991 (4) | 0.1203 (4) | 0.3017 (2) | 0.0417 (12) | 0.50 | | H4 | 0.3239 | 0.0950 | 0.2213 | 0.050* | 0.50 | | C5 | 0.3000 (3) | 0.2975 (3) | 0.3449 (2) | 0.0345 (15) | 0.50 | | H5 | 0.3255 | 0.3933 | 0.2940 | 0.041* | 0.50 | | C6 | 0.2638 (3) | 0.3345 (3) | 0.4624 (3) | 0.0313 (8) | 0.50 | | C7 | 0.2599 (11) | 0.5228 (12) | 0.5056 (7) | 0.0496 (17) | 0.50 | | H7A | 0.3449 | 0.5946 | 0.4761 | 0.074* | 0.50 | | H7B | 0.2932 | 0.5272 | 0.6028 | 0.074* | 0.50 | | H7C | 0.1391 | 0.5719 | 0.4666 | 0.074* | 0.50 | | C8 | 0.3083 (3) | 0.2500 | 0.7686 (2) | 0.0300 (6) | | | C9 | 0.2449 (4) | 0.2500 | 0.8784 (3) | 0.0393 (8) | | | H9 | 0.1194 | 0.2500 | 0.8633 | 0.047* | | | C10 | 0.5314 (3) | 0.2500 | 1.0167 (2) | 0.0284 (6) | | | C11 | 0.6553 (4) | 0.2500 | 1.1448 (3) | 0.0429 (8) | | | H11 | 0.6135 | 0.2500 | 1.2197 | 0.051* | | | C12 | 0.8343 (4) | 0.2500 | 1.1638 (3) | 0.0398 (8) | | | H12 | 0.9169 | 0.2500 | 1.2513 | 0.048* | | | C13 | 0.8952 (4) | 0.2500 | 1.0547 (3) | 0.0631 (12) | | | H13 | 1.0201 | 0.2500 | 1.0674 | 0.076* | | | C14 | 0.7769 (4) | 0.2500 | 0.9289 (3) | 0.0889 (19) | | | H14 | 0.8209 | 0.2500 | 0.8551 | 0.107* | | | C15 | 0.5922 (3) | 0.2500 | 0.9066 (3) | 0.0378 (7) | |
Atomic displacement parameters (Å2) | U11 | U22 | U33 | U12 | U13 | U23 | | O1 | 0.0199 (9) | 0.0771 (16) | 0.0236 (9) | 0.000 | 0.0055 (7) | 0.000 | | N1 | 0.0196 (11) | 0.123 (3) | 0.0224 (12) | 0.000 | 0.0065 (9) | 0.000 | | N2 | 0.0248 (12) | 0.093 (2) | 0.0270 (12) | 0.000 | 0.0090 (9) | 0.000 | | C1 | 0.0198 (14) | 0.033 (2) | 0.0229 (16) | 0.0038 (12) | 0.0051 (12) | 0.0008 (12) | | C2 | 0.057 (4) | 0.056 (5) | 0.031 (3) | 0.004 (3) | 0.018 (3) | 0.002 (3) | | C3 | 0.072 (3) | 0.041 (3) | 0.032 (2) | 0.015 (2) | 0.021 (2) | 0.0047 (19) | | C4 | 0.040 (2) | 0.064 (4) | 0.024 (2) | 0.015 (2) | 0.0142 (17) | 0.002 (2) | | C5 | 0.0231 (15) | 0.054 (5) | 0.0263 (17) | −0.0015 (15) | 0.0075 (13) | 0.0121 (16) | | C6 | 0.0175 (15) | 0.0301 (19) | 0.039 (2) | −0.0008 (15) | −0.0015 (15) | 0.0020 (17) | | C7 | 0.055 (3) | 0.037 (3) | 0.054 (4) | −0.001 (3) | 0.013 (3) | 0.008 (3) | | C8 | 0.0220 (12) | 0.0435 (16) | 0.0233 (12) | 0.000 | 0.0053 (10) | 0.000 | | C9 | 0.0188 (12) | 0.069 (2) | 0.0304 (14) | 0.000 | 0.0084 (11) | 0.000 | | C10 | 0.0230 (12) | 0.0369 (15) | 0.0259 (13) | 0.000 | 0.0086 (10) | 0.000 | | C11 | 0.0303 (14) | 0.076 (2) | 0.0227 (13) | 0.000 | 0.0093 (11) | 0.000 | | C12 | 0.0265 (14) | 0.065 (2) | 0.0243 (13) | 0.000 | 0.0020 (11) | 0.000 | | C13 | 0.0211 (14) | 0.137 (4) | 0.0291 (15) | 0.000 | 0.0053 (12) | 0.000 | | C14 | 0.0238 (15) | 0.221 (6) | 0.0247 (16) | 0.000 | 0.0111 (13) | 0.000 | | C15 | 0.0218 (13) | 0.067 (2) | 0.0236 (13) | 0.000 | 0.0063 (10) | 0.000 |
Geometric parameters (Å, °) | O1—C8 | 1.359 (3) | C6—C7 | 1.472 (9) | | O1—C1 | 1.420 (3) | C7—H7A | 0.9800 | | O1—C1i | 1.420 (3) | C7—H7B | 0.9800 | | N1—C8 | 1.283 (3) | C7—H7C | 0.9800 | | N1—C15 | 1.375 (3) | C8—C9 | 1.402 (4) | | N2—C9 | 1.296 (4) | C9—H9 | 0.9500 | | N2—C10 | 1.369 (3) | C10—C15 | 1.392 (4) | | C1—C2 | 1.3900 | C10—C11 | 1.400 (4) | | C1—C6 | 1.3900 | C11—C12 | 1.360 (4) | | C2—C3 | 1.3900 | C11—H11 | 0.9500 | | C2—H2 | 0.9500 | C12—C13 | 1.384 (4) | | C3—C4 | 1.3900 | C12—H12 | 0.9500 | | C3—H3 | 0.9500 | C13—C14 | 1.365 (4) | | C4—C5 | 1.3900 | C13—H13 | 0.9500 | | C4—H4 | 0.9500 | C14—C15 | 1.398 (4) | | C5—C6 | 1.3900 | C14—H14 | 0.9500 | | C5—H5 | 0.9500 | | | | | | | | C8—O1—C1 | 117.19 (19) | O1—C8—C9 | 114.4 (2) | | C8—N1—C15 | 115.8 (2) | N2—C9—C8 | 122.2 (2) | | C9—N2—C10 | 116.9 (2) | N2—C9—H9 | 118.9 | | C2—C1—C6 | 120.0 | C8—C9—H9 | 118.9 | | C2—C1—O1 | 125.13 (17) | N2—C10—C15 | 120.2 (2) | | C6—C1—O1 | 114.68 (17) | N2—C10—C11 | 120.2 (2) | | C1—C2—C3 | 120.0 | C15—C10—C11 | 119.6 (2) | | C1—C2—H2 | 120.0 | C12—C11—C10 | 121.2 (3) | | C3—C2—H2 | 120.0 | C12—C11—H11 | 119.4 | | C2—C3—C4 | 120.0 | C10—C11—H11 | 119.4 | | C2—C3—H3 | 120.0 | C11—C12—C13 | 119.4 (3) | | C4—C3—H3 | 120.0 | C11—C12—H12 | 120.3 | | C5—C4—C3 | 120.0 | C13—C12—H12 | 120.3 | | C5—C4—H4 | 120.0 | C14—C13—C12 | 120.4 (3) | | C3—C4—H4 | 120.0 | C14—C13—H13 | 119.8 | | C4—C5—C6 | 120.0 | C12—C13—H13 | 119.8 | | C4—C5—H5 | 120.0 | C13—C14—C15 | 121.3 (3) | | C6—C5—H5 | 120.0 | C13—C14—H14 | 119.4 | | C5—C6—C1 | 120.0 | C15—C14—H14 | 119.4 | | C5—C6—C7 | 119.7 (3) | N1—C15—C10 | 121.5 (2) | | C1—C6—C7 | 120.3 (3) | N1—C15—C14 | 120.4 (2) | | N1—C8—O1 | 122.3 (2) | C10—C15—C14 | 118.1 (3) | | N1—C8—C9 | 123.4 (2) | | | | | | | | C8—O1—C1—C2 | 87.53 (18) | C1i—O1—C8—C9 | 160.91 (12) | | C1i—O1—C1—C2 | −173.48 (14) | C10—N2—C9—C8 | 0.000 (2) | | C8—O1—C1—C6 | −97.56 (16) | N1—C8—C9—N2 | 0.000 (2) | | C1i—O1—C1—C6 | 1.43 (19) | O1—C8—C9—N2 | 180.000 (1) | | C6—C1—C2—C3 | 0.0 | C9—N2—C10—C15 | 0.000 (2) | | O1—C1—C2—C3 | 174.7 (2) | C9—N2—C10—C11 | 180.000 (2) | | C1—C2—C3—C4 | 0.0 | N2—C10—C11—C12 | 180.000 (2) | | C2—C3—C4—C5 | 0.0 | C15—C10—C11—C12 | 0.000 (2) | | C3—C4—C5—C6 | 0.0 | C10—C11—C12—C13 | 0.000 (2) | | C4—C5—C6—C1 | 0.0 | C11—C12—C13—C14 | 0.000 (2) | | C4—C5—C6—C7 | −178.3 (4) | C12—C13—C14—C15 | 0.000 (2) | | C2—C1—C6—C5 | 0.0 | C8—N1—C15—C10 | 0.000 (1) | | O1—C1—C6—C5 | −175.2 (2) | C8—N1—C15—C14 | 180.000 (1) | | C2—C1—C6—C7 | 178.2 (4) | N2—C10—C15—N1 | 0.000 (2) | | O1—C1—C6—C7 | 3.0 (4) | C11—C10—C15—N1 | 180.000 (1) | | C15—N1—C8—O1 | 180.000 (1) | N2—C10—C15—C14 | 180.000 (2) | | C15—N1—C8—C9 | 0.000 (1) | C11—C10—C15—C14 | 0.000 (2) | | C1—O1—C8—N1 | 19.09 (12) | C13—C14—C15—N1 | 180.000 (2) | | C1i—O1—C8—N1 | −19.09 (12) | C13—C14—C15—C10 | 0.000 (2) | | C1—O1—C8—C9 | −160.91 (12) | | |
Symmetry codes: (i) x, −y+1/2, z. - Abdullah, Z. (2005). Int. J. Chem. Sci.3, 9–15.
- Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
- Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
- Kawai, M., Lee, M. J., Evans, K. O. & Norlund, T. (2001). J. Fluoresc.11, 23–32.
- Mohd Salleh, N., Ling, L. P., Abdullah, Z. M. A. A. & Aiyub, Z. (2007). Malays. J. Anal. Sci.11, 229–236.
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
- Westrip, S. P. (2008). publCIF In preparation.
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