|
|
Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1820. | PMCID: PMC2960479 |
Phenyl quinoxalin-2-yl 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 18, 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 aromatic ring systems in the title compound, C14H10N2O, form a dihedral angle of 63.8 (1)°, resulting in an opening up of the ether-O atom angle to 118.2 (1)°. The title compound exhibits fluorescence; see: Abdullah (2005 ![[triangle]](/corehtml/pmc/pmcents/rtrif.gif) ); Kawai et al. (2001 ); Mohd Salleh et al. (2007 ). For the only previously reported structural example of a quinoxalinoxy compound, see: Csikós et al. (1999 ). Click on image to enlarge  Crystal data
- C14H10N2O
-
M
r = 222.24
- Monoclinic,
-
a = 18.175 (2) Å
-
b = 6.6589 (8) Å
-
c = 19.488 (2) Å
- β = 112.937 (2)°
-
V = 2172.1 (5) Å3
-
Z = 8
- Mo Kα radiation
- μ = 0.09 mm−1
-
T = 100 (2) K
- 0.30 × 0.20 × 0.05 mm
Data collection
- Bruker SMART APEX diffractometer
- Absorption correction: none
- 6018 measured reflections
- 2478 independent reflections
- 1909 reflections with I > 2σ(I)
-
R
int = 0.026
Refinement
-
R[F
2 > 2σ(F
2)] = 0.039
-
wR(F
2) = 0.104
-
S = 1.07
- 2478 reflections
- 154 parameters
- H-atom parameters constrained
- Δρmax = 0.27 e Å−3
- Δρmin = −0.27 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 Phenol (0.47 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 of (I).
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) fixed at 1.2U(C). Crystal data | C14H10N2O | F000 = 928 | | Mr = 222.24 | Dx = 1.359 Mg m−3 | | Monoclinic, C2/c | Mo Kα radiation λ = 0.71073 Å | | Hall symbol: -C 2yc | Cell parameters from 1614 reflections | | a = 18.175 (2) Å | θ = 2.4–28.2º | | b = 6.6589 (8) Å | µ = 0.09 mm−1 | | c = 19.488 (2) Å | T = 100 (2) K | | β = 112.937 (2)º | Prism, colorless | | V = 2172.1 (5) Å3 | 0.30 × 0.20 × 0.05 mm | | Z = 8 | |
Data collection | Bruker SMART APEX diffractometer | 1909 reflections with I > 2σ(I) | | Radiation source: fine-focus sealed tube | Rint = 0.026 | | Monochromator: graphite | θmax = 27.5º | | T = 100(2) K | θmin = 2.3º | | ω scans | h = −23→16 | | Absorption correction: None | k = −8→8 | | 6018 measured reflections | l = −23→25 | | 2478 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)] = 0.039 | H-atom parameters constrained | | wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0479P)2 + 0.7132P] where P = (Fo2 + 2Fc2)/3 | | S = 1.07 | (Δ/σ)max = 0.001 | | 2478 reflections | Δρmax = 0.27 e Å−3 | | 154 parameters | Δρmin = −0.27 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 | | | O1 | 0.68658 (5) | 0.68613 (14) | 0.55215 (5) | 0.0196 (2) | | | N1 | 0.59181 (6) | 0.76551 (15) | 0.59977 (6) | 0.0166 (2) | | | N2 | 0.47638 (6) | 0.72591 (16) | 0.45219 (6) | 0.0176 (2) | | | C1 | 0.74734 (7) | 0.7128 (2) | 0.62327 (7) | 0.0178 (3) | | | C2 | 0.75301 (8) | 0.5866 (2) | 0.68141 (8) | 0.0242 (3) | | | H2 | 0.7143 | 0.4846 | 0.6749 | 0.029* | | | C3 | 0.81628 (9) | 0.6118 (2) | 0.74933 (8) | 0.0291 (4) | | | H3 | 0.8209 | 0.5269 | 0.7900 | 0.035* | | | C4 | 0.87301 (9) | 0.7599 (2) | 0.75850 (8) | 0.0293 (4) | | | H4 | 0.9163 | 0.7763 | 0.8053 | 0.035* | | | C5 | 0.86637 (8) | 0.8838 (2) | 0.69930 (8) | 0.0267 (3) | | | H5 | 0.9053 | 0.9849 | 0.7055 | 0.032* | | | C6 | 0.80290 (8) | 0.8608 (2) | 0.63088 (7) | 0.0208 (3) | | | H6 | 0.7980 | 0.9456 | 0.5901 | 0.025* | | | C7 | 0.60973 (7) | 0.71759 (18) | 0.54400 (7) | 0.0167 (3) | | | C8 | 0.55218 (8) | 0.69640 (19) | 0.46909 (7) | 0.0180 (3) | | | H8 | 0.5698 | 0.6599 | 0.4309 | 0.022* | | | C9 | 0.45400 (7) | 0.77709 (18) | 0.50983 (7) | 0.0156 (3) | | | C10 | 0.37309 (8) | 0.81243 (19) | 0.49536 (7) | 0.0184 (3) | | | H10 | 0.3341 | 0.8006 | 0.4460 | 0.022* | | | C11 | 0.35029 (8) | 0.86377 (19) | 0.55218 (7) | 0.0202 (3) | | | H11 | 0.2955 | 0.8882 | 0.5420 | 0.024* | | | C12 | 0.40760 (8) | 0.8806 (2) | 0.62563 (7) | 0.0204 (3) | | | H12 | 0.3912 | 0.9162 | 0.6647 | 0.025* | | | C13 | 0.48681 (8) | 0.8460 (2) | 0.64120 (7) | 0.0189 (3) | | | H13 | 0.5249 | 0.8564 | 0.6910 | 0.023* | | | C14 | 0.51180 (7) | 0.79510 (18) | 0.58369 (7) | 0.0157 (3) | |
Atomic displacement parameters (Å2) | U11 | U22 | U33 | U12 | U13 | U23 | | O1 | 0.0157 (5) | 0.0261 (5) | 0.0182 (5) | 0.0021 (4) | 0.0079 (4) | −0.0013 (4) | | N1 | 0.0167 (6) | 0.0160 (5) | 0.0179 (5) | −0.0007 (4) | 0.0077 (4) | −0.0009 (4) | | N2 | 0.0214 (6) | 0.0154 (5) | 0.0166 (5) | −0.0008 (4) | 0.0079 (4) | −0.0009 (4) | | C1 | 0.0158 (6) | 0.0218 (6) | 0.0172 (6) | 0.0052 (5) | 0.0079 (5) | −0.0004 (5) | | C2 | 0.0238 (7) | 0.0257 (7) | 0.0295 (7) | 0.0071 (6) | 0.0174 (6) | 0.0064 (6) | | C3 | 0.0297 (8) | 0.0404 (9) | 0.0233 (7) | 0.0181 (7) | 0.0169 (6) | 0.0118 (6) | | C4 | 0.0222 (7) | 0.0439 (9) | 0.0184 (7) | 0.0127 (7) | 0.0045 (6) | −0.0019 (6) | | C5 | 0.0208 (7) | 0.0291 (7) | 0.0277 (7) | 0.0011 (6) | 0.0067 (6) | −0.0045 (6) | | C6 | 0.0196 (7) | 0.0228 (7) | 0.0215 (7) | 0.0036 (5) | 0.0097 (6) | 0.0029 (5) | | C7 | 0.0161 (6) | 0.0148 (6) | 0.0208 (6) | −0.0003 (5) | 0.0090 (5) | 0.0005 (5) | | C8 | 0.0221 (7) | 0.0164 (6) | 0.0176 (6) | −0.0006 (5) | 0.0102 (5) | −0.0007 (5) | | C9 | 0.0182 (6) | 0.0120 (6) | 0.0170 (6) | −0.0008 (5) | 0.0074 (5) | −0.0006 (5) | | C10 | 0.0177 (7) | 0.0159 (6) | 0.0185 (6) | −0.0008 (5) | 0.0037 (5) | 0.0000 (5) | | C11 | 0.0149 (6) | 0.0189 (6) | 0.0270 (7) | 0.0001 (5) | 0.0084 (5) | 0.0006 (5) | | C12 | 0.0220 (7) | 0.0213 (6) | 0.0215 (6) | −0.0001 (5) | 0.0123 (6) | −0.0019 (5) | | C13 | 0.0196 (7) | 0.0205 (6) | 0.0168 (6) | −0.0005 (5) | 0.0072 (5) | −0.0009 (5) | | C14 | 0.0152 (6) | 0.0133 (6) | 0.0184 (6) | −0.0006 (5) | 0.0062 (5) | 0.0003 (5) |
Geometric parameters (Å, °) | O1—C7 | 1.3591 (15) | C5—H5 | 0.9500 | | O1—C1 | 1.4068 (15) | C6—H6 | 0.9500 | | N1—C7 | 1.2904 (17) | C7—C8 | 1.4335 (17) | | N1—C14 | 1.3771 (16) | C8—H8 | 0.9500 | | N2—C8 | 1.3006 (17) | C9—C10 | 1.4051 (18) | | N2—C9 | 1.3782 (17) | C9—C14 | 1.4182 (17) | | C1—C6 | 1.3769 (19) | C10—C11 | 1.3685 (19) | | C1—C2 | 1.3821 (18) | C10—H10 | 0.9500 | | C2—C3 | 1.384 (2) | C11—C12 | 1.4086 (18) | | C2—H2 | 0.9500 | C11—H11 | 0.9500 | | C3—C4 | 1.387 (2) | C12—C13 | 1.3703 (18) | | C3—H3 | 0.9500 | C12—H12 | 0.9500 | | C4—C5 | 1.385 (2) | C13—C14 | 1.4048 (18) | | C4—H4 | 0.9500 | C13—H13 | 0.9500 | | C5—C6 | 1.3903 (18) | | | | | | | | C7—O1—C1 | 118.16 (10) | O1—C7—C8 | 114.37 (11) | | C7—N1—C14 | 115.75 (11) | N2—C8—C7 | 121.57 (12) | | C8—N2—C9 | 116.80 (11) | N2—C8—H8 | 119.2 | | C6—C1—C2 | 121.99 (12) | C7—C8—H8 | 119.2 | | C6—C1—O1 | 117.24 (11) | N2—C9—C10 | 119.73 (11) | | C2—C1—O1 | 120.65 (12) | N2—C9—C14 | 120.73 (12) | | C1—C2—C3 | 118.61 (14) | C10—C9—C14 | 119.54 (12) | | C1—C2—H2 | 120.7 | C11—C10—C9 | 120.18 (12) | | C3—C2—H2 | 120.7 | C11—C10—H10 | 119.9 | | C2—C3—C4 | 120.54 (13) | C9—C10—H10 | 119.9 | | C2—C3—H3 | 119.7 | C10—C11—C12 | 120.33 (12) | | C4—C3—H3 | 119.7 | C10—C11—H11 | 119.8 | | C5—C4—C3 | 119.82 (13) | C12—C11—H11 | 119.8 | | C5—C4—H4 | 120.1 | C13—C12—C11 | 120.57 (12) | | C3—C4—H4 | 120.1 | C13—C12—H12 | 119.7 | | C4—C5—C6 | 120.25 (14) | C11—C12—H12 | 119.7 | | C4—C5—H5 | 119.9 | C12—C13—C14 | 120.16 (12) | | C6—C5—H5 | 119.9 | C12—C13—H13 | 119.9 | | C1—C6—C5 | 118.80 (13) | C14—C13—H13 | 119.9 | | C1—C6—H6 | 120.6 | N1—C14—C13 | 119.60 (11) | | C5—C6—H6 | 120.6 | N1—C14—C9 | 121.18 (12) | | N1—C7—O1 | 121.67 (11) | C13—C14—C9 | 119.22 (12) | | N1—C7—C8 | 123.96 (12) | | | | | | | | C7—O1—C1—C6 | −117.62 (13) | O1—C7—C8—N2 | −178.58 (11) | | C7—O1—C1—C2 | 66.18 (16) | C8—N2—C9—C10 | 179.57 (11) | | C6—C1—C2—C3 | 0.5 (2) | C8—N2—C9—C14 | −0.26 (17) | | O1—C1—C2—C3 | 176.56 (12) | N2—C9—C10—C11 | −179.85 (12) | | C1—C2—C3—C4 | −0.4 (2) | C14—C9—C10—C11 | −0.03 (19) | | C2—C3—C4—C5 | 0.0 (2) | C9—C10—C11—C12 | −0.3 (2) | | C3—C4—C5—C6 | 0.3 (2) | C10—C11—C12—C13 | 0.0 (2) | | C2—C1—C6—C5 | −0.2 (2) | C11—C12—C13—C14 | 0.6 (2) | | O1—C1—C6—C5 | −176.37 (11) | C7—N1—C14—C13 | 179.44 (12) | | C4—C5—C6—C1 | −0.2 (2) | C7—N1—C14—C9 | −1.19 (17) | | C14—N1—C7—O1 | 179.35 (11) | C12—C13—C14—N1 | 178.41 (11) | | C14—N1—C7—C8 | 0.49 (18) | C12—C13—C14—C9 | −0.98 (19) | | C1—O1—C7—N1 | −1.81 (18) | N2—C9—C14—N1 | 1.12 (18) | | C1—O1—C7—C8 | 177.15 (10) | C10—C9—C14—N1 | −178.70 (11) | | C9—N2—C8—C7 | −0.45 (18) | N2—C9—C14—C13 | −179.50 (12) | | N1—C7—C8—N2 | 0.3 (2) | C10—C9—C14—C13 | 0.68 (18) |
- 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.
- Csikós, É., Ferenczy, G. G., Ángyán, J. G., Böcskei, Z., Simon, K., Gönczi, C., Hermecz, I. & Hermecz, I. (1999). Eur. J. Org. Chem. pp. 2119–2125.
- 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.
|
