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The two aromatic systems in the title compound, C14H10N2O, enclose a dihedral angle of 77.9 (1)°, and the C-O-C inter-ring bond angle is 117.6 (1)°.
Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808031243/im2084sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808031243/im2084Isup2.hkl |
CCDC reference: 709396
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
![[sigma]](https://journals.iucr.org/logos/entities/sigma_rmgif.gif)
(C-C) = 0.002 Å - R factor = 0.037
- wR factor = 0.114
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT112_ALERT_2_B ADDSYM Detects Additional (Pseudo) Symm. Elem... B
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Experimental top
The monoclinic modification was obtained when the C2/c modification of quinoxalinyl phenyl ether was recrystallized from ethanol in the presence of a small quantity of manganese acetate. Slow evaporation of the solvent gave colorless crystals mixed with unchanged manganese acetate.
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) fixed at 1.2U(C).
Computing details top
Data collection: APEX2 or SMART? (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, 2008).
Figures top
![[Figure 1]](https://journals.iucr.org/e/issues/2008/11/00/im2084/im2084fig1thm.gif)
| Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C14H10N2O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. |
phenyl quinoxalin-2-yl ether top
Crystal data top
| C14H10N2O | F(000) = 464 |
| Mr = 222.24 | Dx = 1.405 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 2712 reflections |
| a = 7.9447 (2) Å | θ = 2.7–28.4° |
| b = 6.5169 (1) Å | µ = 0.09 mm−1 |
| c = 20.2992 (5) Å | T = 100 K |
| β = 91.983 (1)° | Block, colorless |
| V = 1050.36 (4) Å3 | 0.40 × 0.20 × 0.10 mm |
| Z = 4 |
Data collection top
| Bruker SMART APEX diffractometer | 1960 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.021 |
| Graphite monochromator | θmax = 27.5°, θmin = 2.0° |
| ω scans | h = −10→9 |
| 7016 measured reflections | k = −8→8 |
| 2398 independent reflections | l = −26→26 |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.114 | H-atom parameters constrained |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.0648P)2 + 0.2602P] where P = (Fo2 + 2Fc2)/3 |
| 2398 reflections | (Δ/σ)max = 0.001 |
| 154 parameters | Δρmax = 0.33 e Å−3 |
| 0 restraints | Δρmin = −0.23 e Å−3 |
Crystal data top
| C14H10N2O | V = 1050.36 (4) Å3 |
| Mr = 222.24 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 7.9447 (2) Å | µ = 0.09 mm−1 |
| b = 6.5169 (1) Å | T = 100 K |
| c = 20.2992 (5) Å | 0.40 × 0.20 × 0.10 mm |
| β = 91.983 (1)° |
Data collection top
| Bruker SMART APEX diffractometer | 1960 reflections with I > 2σ(I) |
| 7016 measured reflections | Rint = 0.021 |
| 2398 independent reflections |
Refinement top
| R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
| wR(F2) = 0.114 | H-atom parameters constrained |
| S = 1.03 | Δρmax = 0.33 e Å−3 |
| 2398 reflections | Δρmin = −0.23 e Å−3 |
| 154 parameters |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.34884 (10) | 0.24973 (13) | 0.66577 (4) | 0.0189 (2) | |
| N1 | 0.58503 (12) | 0.26591 (14) | 0.60174 (5) | 0.0150 (2) | |
| N2 | 0.35723 (12) | 0.23610 (14) | 0.49088 (5) | 0.0153 (2) | |
| C1 | 0.45193 (13) | 0.28653 (19) | 0.72247 (5) | 0.0170 (3) | |
| C2 | 0.44960 (15) | 0.48057 (19) | 0.74939 (6) | 0.0199 (3) | |
| H2 | 0.3836 | 0.5863 | 0.7292 | 0.024* | |
| C3 | 0.54551 (15) | 0.5187 (2) | 0.80653 (6) | 0.0233 (3) | |
| H3 | 0.5461 | 0.6519 | 0.8255 | 0.028* | |
| C4 | 0.64037 (15) | 0.3635 (2) | 0.83596 (6) | 0.0232 (3) | |
| H4 | 0.7066 | 0.3906 | 0.8749 | 0.028* | |
| C5 | 0.63876 (15) | 0.1689 (2) | 0.80870 (6) | 0.0242 (3) | |
| H5 | 0.7029 | 0.0622 | 0.8293 | 0.029* | |
| C6 | 0.54360 (15) | 0.1286 (2) | 0.75122 (6) | 0.0219 (3) | |
| H6 | 0.5419 | −0.0047 | 0.7323 | 0.026* | |
| C7 | 0.42352 (15) | 0.25028 (16) | 0.60650 (5) | 0.0148 (2) | |
| C8 | 0.30741 (14) | 0.23391 (17) | 0.55103 (6) | 0.0158 (3) | |
| H8 | 0.1905 | 0.2211 | 0.5586 | 0.019* | |
| C9 | 0.52855 (14) | 0.25143 (16) | 0.48299 (5) | 0.0139 (2) | |
| C10 | 0.59172 (15) | 0.25296 (17) | 0.41912 (5) | 0.0160 (3) | |
| H10 | 0.5161 | 0.2467 | 0.3819 | 0.019* | |
| C11 | 0.76232 (15) | 0.26345 (17) | 0.41025 (6) | 0.0174 (3) | |
| H11 | 0.8043 | 0.2630 | 0.3670 | 0.021* | |
| C12 | 0.87492 (15) | 0.27483 (18) | 0.46528 (6) | 0.0179 (3) | |
| H12 | 0.9927 | 0.2808 | 0.4589 | 0.021* | |
| C13 | 0.81557 (14) | 0.27741 (18) | 0.52800 (6) | 0.0167 (3) | |
| H13 | 0.8925 | 0.2878 | 0.5647 | 0.020* | |
| C14 | 0.64163 (14) | 0.26477 (16) | 0.53833 (5) | 0.0141 (2) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0148 (4) | 0.0292 (5) | 0.0127 (4) | −0.0019 (3) | 0.0008 (3) | −0.0024 (3) |
| N1 | 0.0146 (5) | 0.0160 (5) | 0.0144 (5) | 0.0003 (3) | −0.0008 (4) | −0.0002 (3) |
| N2 | 0.0155 (5) | 0.0137 (5) | 0.0166 (5) | 0.0004 (3) | −0.0011 (4) | −0.0005 (4) |
| C1 | 0.0119 (5) | 0.0277 (6) | 0.0116 (5) | −0.0025 (4) | 0.0025 (4) | 0.0000 (4) |
| C2 | 0.0208 (6) | 0.0237 (6) | 0.0153 (5) | −0.0008 (5) | 0.0014 (4) | 0.0026 (4) |
| C3 | 0.0253 (6) | 0.0276 (7) | 0.0170 (6) | −0.0061 (5) | 0.0017 (5) | −0.0019 (5) |
| C4 | 0.0160 (6) | 0.0396 (8) | 0.0140 (5) | −0.0056 (5) | 0.0002 (4) | 0.0014 (5) |
| C5 | 0.0164 (6) | 0.0368 (7) | 0.0195 (6) | 0.0047 (5) | 0.0025 (4) | 0.0076 (5) |
| C6 | 0.0199 (6) | 0.0262 (7) | 0.0199 (6) | 0.0018 (5) | 0.0042 (4) | −0.0001 (5) |
| C7 | 0.0168 (5) | 0.0137 (5) | 0.0139 (5) | 0.0000 (4) | 0.0014 (4) | −0.0007 (4) |
| C8 | 0.0134 (5) | 0.0162 (6) | 0.0177 (6) | 0.0003 (4) | −0.0005 (4) | −0.0009 (4) |
| C9 | 0.0146 (5) | 0.0113 (5) | 0.0158 (6) | 0.0011 (4) | −0.0008 (4) | 0.0001 (4) |
| C10 | 0.0188 (6) | 0.0148 (6) | 0.0142 (5) | 0.0015 (4) | −0.0024 (4) | 0.0002 (4) |
| C11 | 0.0200 (6) | 0.0186 (6) | 0.0138 (5) | 0.0017 (4) | 0.0030 (4) | 0.0013 (4) |
| C12 | 0.0147 (5) | 0.0195 (6) | 0.0196 (6) | 0.0009 (4) | 0.0023 (4) | 0.0011 (4) |
| C13 | 0.0145 (5) | 0.0192 (6) | 0.0161 (6) | 0.0009 (4) | −0.0020 (4) | 0.0007 (4) |
| C14 | 0.0158 (6) | 0.0121 (5) | 0.0142 (5) | 0.0007 (4) | −0.0002 (4) | 0.0005 (4) |
Geometric parameters (Å, º) top
| O1—C7 | 1.3598 (14) | C5—H5 | 0.9500 |
| O1—C1 | 1.4099 (13) | C6—H6 | 0.9500 |
| N1—C7 | 1.2941 (15) | C7—C8 | 1.4346 (15) |
| N1—C14 | 1.3781 (14) | C8—H8 | 0.9500 |
| N2—C8 | 1.2966 (15) | C9—C10 | 1.4066 (15) |
| N2—C9 | 1.3796 (15) | C9—C14 | 1.4165 (16) |
| C1—C2 | 1.3780 (17) | C10—C11 | 1.3751 (16) |
| C1—C6 | 1.3786 (17) | C10—H10 | 0.9500 |
| C2—C3 | 1.3880 (16) | C11—C12 | 1.4086 (16) |
| C2—H2 | 0.9500 | C11—H11 | 0.9500 |
| C3—C4 | 1.3847 (18) | C12—C13 | 1.3730 (15) |
| C3—H3 | 0.9500 | C12—H12 | 0.9500 |
| C4—C5 | 1.383 (2) | C13—C14 | 1.4073 (16) |
| C4—H4 | 0.9500 | C13—H13 | 0.9500 |
| C5—C6 | 1.3931 (17) | ||
| C7—O1—C1 | 117.58 (9) | O1—C7—C8 | 113.94 (10) |
| C7—N1—C14 | 115.20 (10) | N2—C8—C7 | 121.96 (11) |
| C8—N2—C9 | 116.40 (10) | N2—C8—H8 | 119.0 |
| C2—C1—C6 | 122.08 (11) | C7—C8—H8 | 119.0 |
| C2—C1—O1 | 117.68 (10) | N2—C9—C10 | 119.51 (10) |
| C6—C1—O1 | 120.14 (11) | N2—C9—C14 | 120.90 (10) |
| C1—C2—C3 | 118.77 (11) | C10—C9—C14 | 119.59 (10) |
| C1—C2—H2 | 120.6 | C11—C10—C9 | 120.38 (10) |
| C3—C2—H2 | 120.6 | C11—C10—H10 | 119.8 |
| C4—C3—C2 | 120.30 (12) | C9—C10—H10 | 119.8 |
| C4—C3—H3 | 119.8 | C10—C11—C12 | 120.04 (11) |
| C2—C3—H3 | 119.8 | C10—C11—H11 | 120.0 |
| C5—C4—C3 | 119.98 (11) | C12—C11—H11 | 120.0 |
| C5—C4—H4 | 120.0 | C13—C12—C11 | 120.46 (11) |
| C3—C4—H4 | 120.0 | C13—C12—H12 | 119.8 |
| C4—C5—C6 | 120.32 (12) | C11—C12—H12 | 119.8 |
| C4—C5—H5 | 119.8 | C12—C13—C14 | 120.53 (10) |
| C6—C5—H5 | 119.8 | C12—C13—H13 | 119.7 |
| C1—C6—C5 | 118.53 (12) | C14—C13—H13 | 119.7 |
| C1—C6—H6 | 120.7 | N1—C14—C13 | 119.52 (10) |
| C5—C6—H6 | 120.7 | N1—C14—C9 | 121.50 (10) |
| N1—C7—O1 | 122.03 (10) | C13—C14—C9 | 118.98 (11) |
| N1—C7—C8 | 124.02 (11) | ||
| C7—O1—C1—C2 | 100.70 (12) | O1—C7—C8—N2 | 178.65 (10) |
| C7—O1—C1—C6 | −82.79 (13) | C8—N2—C9—C10 | 179.47 (10) |
| C6—C1—C2—C3 | 1.36 (17) | C8—N2—C9—C14 | −0.26 (15) |
| O1—C1—C2—C3 | 177.79 (10) | N2—C9—C10—C11 | −178.53 (10) |
| C1—C2—C3—C4 | −0.52 (17) | C14—C9—C10—C11 | 1.21 (16) |
| C2—C3—C4—C5 | −0.52 (18) | C9—C10—C11—C12 | −0.64 (16) |
| C3—C4—C5—C6 | 0.77 (18) | C10—C11—C12—C13 | −0.59 (17) |
| C2—C1—C6—C5 | −1.11 (17) | C11—C12—C13—C14 | 1.22 (17) |
| O1—C1—C6—C5 | −177.45 (10) | C7—N1—C14—C13 | −178.90 (10) |
| C4—C5—C6—C1 | 0.02 (17) | C7—N1—C14—C9 | 1.19 (15) |
| C14—N1—C7—O1 | −179.82 (10) | C12—C13—C14—N1 | 179.46 (10) |
| C14—N1—C7—C8 | −0.37 (15) | C12—C13—C14—C9 | −0.63 (16) |
| C1—O1—C7—N1 | 5.91 (15) | N2—C9—C14—N1 | −0.94 (16) |
| C1—O1—C7—C8 | −173.59 (10) | C10—C9—C14—N1 | 179.33 (10) |
| C9—N2—C8—C7 | 1.10 (15) | N2—C9—C14—C13 | 179.15 (10) |
| N1—C7—C8—N2 | −0.84 (17) | C10—C9—C14—C13 | −0.58 (15) |
Experimental details
| Crystal data | |
| Chemical formula | C14H10N2O |
| Mr | 222.24 |
| Crystal system, space group | Monoclinic, P21/n |
| Temperature (K) | 100 |
| a, b, c (Å) | 7.9447 (2), 6.5169 (1), 20.2992 (5) |
| β (°) | 91.983 (1) |
| V (Å3) | 1050.36 (4) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.09 |
| Crystal size (mm) | 0.40 × 0.20 × 0.10 |
| Data collection | |
| Diffractometer | Bruker SMART APEX diffractometer |
| Absorption correction | – |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 7016, 2398, 1960 |
| Rint | 0.021 |
| (sin θ/λ)max (Å−1) | 0.650 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.114, 1.03 |
| No. of reflections | 2398 |
| No. of parameters | 154 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.33, −0.23 |
Computer programs: APEX2 or SMART? (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).
The compound was recently described in the C2/c space group with the two aromatic substituents in C14H10N2O enclosing a dihedral angle of 63.8 (1)°. The bond angle at oxygen measures to 118.2 (1)° (Hassan et al., 2008). In the P21/n modification described herein (Scheme I, Fig. 1), the two aromatic systems show a dihedral angle of 77.9 (1)° and they subtend an angle of 117.6 (1)° at oxygen.