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access3,4-Dimethyl-N-[(E)-3-nitrobenzylidene]-1,2-oxazol-5-amine
aThe Center of Excellence for Advanced Materials Research, King Abdul Aziz University, Jeddah 21589, PO Box 80203, Saudi Arabia, bDepartment of Chemistry, Faculty of Science, King Abdul Aziz University, Jeddah 21589, PO Box 80203, Saudi Arabia, and cDepartment of Physics, University of Sargodha, Sargodha, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com
In the title compound, C12H11N3O3, the dihedral angle between the 3-nitrobenzaldehyde and 5-amino-3,4-dimethyl-1,2-oxazole moieties is 2.46 (12)°. The molecule is close to planar, the r.m.s. deviation for the non-H atoms being 0.028 Å. The packing only features van der Waals interactions between the molecules.
![[Scheme 1]](hb5634scheme1.gif)
Experimental
Crystal data
|
Data collection: APEX2 (Bruker, 2009![[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]](../../../../../../logos/arrows/e_arr.gif "Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.")
); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.
Supporting information
contains datablocks global, I. DOI: 10.1107/S160053681003583X/hb5634sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S160053681003583X/hb5634Isup2.hkl
A mixture of 4-nitrobenzaldehyde (0.33 g, 2.2 mmol) and 5-amino-3,4-dimethylisoxazole (0.24 g, 2.2 mmol) in ethanol (15 ml) was refluxed for 5 h with stirring to give a light yellow precipitate. This material was filtered off and washed with ethanol to give long thin needles of (I).
Yield: 56.45%; m.p. 463–464 K.
IR (KBr) \vmax cm-1: 3069 (C—H for CH3), 2922 (C—H), 1568 (C═C), 1523 (C═N), 1162 (C—N).
The H-atoms were positioned geometrically (C–H = 0.93–0.96 Å) and refined as riding with Uiso(H) = xUeq(C), where x = 1.5 for methyl and x = 1.2 for other H-atoms.
Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
![[Figure 1]](./hb5634fig1thm.gif)
| C12H11N3O3 | F(000) = 512 |
| Mr = 245.24 | Dx = 1.414 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 846 reflections |
| a = 12.602 (2) Å | θ = 2.3–25.0° |
| b = 3.9267 (6) Å | µ = 0.11 mm−1 |
| c = 23.366 (4) Å | T = 296 K |
| β = 94.791 (9)° | Needle, colorless |
| V = 1152.3 (3) Å3 | 0.22 × 0.08 × 0.06 mm |
| Z = 4 |
| Bruker Kappa APEXII CCD diffractometer | 2046 independent reflections |
| Radiation source: fine-focus sealed tube | 846 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.097 |
| Detector resolution: 8.20 pixels mm-1 | θmax = 25.0°, θmin = 2.3° |
| ω scans | h = −15→15 |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −4→4 |
| Tmin = 0.992, Tmax = 0.995 | l = −27→27 |
| 8616 measured reflections |
| 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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.161 | H-atom parameters constrained |
| S = 0.99 | w = 1/[σ2(Fo2) + (0.0341P)2] where P = (Fo2 + 2Fc2)/3 |
| 2046 reflections | (Δ/σ)max < 0.001 |
| 166 parameters | Δρmax = 0.16 e Å−3 |
| 0 restraints | Δρmin = −0.19 e Å−3 |
| C12H11N3O3 | V = 1152.3 (3) Å3 |
| Mr = 245.24 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 12.602 (2) Å | µ = 0.11 mm−1 |
| b = 3.9267 (6) Å | T = 296 K |
| c = 23.366 (4) Å | 0.22 × 0.08 × 0.06 mm |
| β = 94.791 (9)° |
| Bruker Kappa APEXII CCD diffractometer | 2046 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | 846 reflections with I > 2σ(I) |
| Tmin = 0.992, Tmax = 0.995 | Rint = 0.097 |
| 8616 measured reflections |
| R[F2 > 2σ(F2)] = 0.061 | 0 restraints |
| wR(F2) = 0.161 | H-atom parameters constrained |
| S = 0.99 | Δρmax = 0.16 e Å−3 |
| 2046 reflections | Δρmin = −0.19 e Å−3 |
| 166 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.0661 (2) | 0.9618 (9) | 0.11316 (16) | 0.0932 (16) | |
| O2 | 0.0217 (3) | 0.7756 (9) | 0.19373 (16) | 0.1103 (19) | |
| O3 | 0.5961 (2) | 0.7628 (6) | 0.02581 (12) | 0.0630 (11) | |
| N1 | 0.0873 (3) | 0.8153 (10) | 0.15894 (19) | 0.0708 (17) | |
| N2 | 0.5490 (3) | 0.5694 (8) | 0.11691 (13) | 0.0523 (12) | |
| N3 | 0.6882 (3) | 0.7702 (8) | −0.00509 (15) | 0.0660 (17) | |
| C1 | 0.3736 (3) | 0.6218 (9) | 0.14659 (17) | 0.0475 (17) | |
| C2 | 0.3985 (3) | 0.4605 (10) | 0.19866 (18) | 0.0579 (17) | |
| C3 | 0.3218 (4) | 0.4146 (10) | 0.23763 (18) | 0.0629 (17) | |
| C4 | 0.2194 (4) | 0.5255 (10) | 0.22380 (19) | 0.0618 (17) | |
| C5 | 0.1954 (3) | 0.6856 (10) | 0.17248 (19) | 0.0534 (17) | |
| C6 | 0.2697 (3) | 0.7379 (9) | 0.13294 (17) | 0.0511 (17) | |
| C7 | 0.4530 (3) | 0.6720 (9) | 0.10518 (17) | 0.0527 (17) | |
| C8 | 0.6232 (3) | 0.6142 (10) | 0.07766 (17) | 0.0521 (17) | |
| C9 | 0.7266 (3) | 0.5238 (9) | 0.08165 (17) | 0.0485 (17) | |
| C10 | 0.7629 (3) | 0.6275 (9) | 0.02938 (19) | 0.0513 (17) | |
| C11 | 0.8723 (3) | 0.5881 (10) | 0.00968 (19) | 0.0727 (19) | |
| C12 | 0.7889 (3) | 0.3614 (10) | 0.13104 (17) | 0.0672 (17) | |
| H2 | 0.46743 | 0.38159 | 0.20778 | 0.0695* | |
| H3 | 0.33974 | 0.30952 | 0.27277 | 0.0758* | |
| H4 | 0.16713 | 0.49195 | 0.24908 | 0.0742* | |
| H6 | 0.25095 | 0.84733 | 0.09826 | 0.0611* | |
| H7 | 0.43386 | 0.77846 | 0.07029 | 0.0629* | |
| H11A | 0.87321 | 0.67477 | −0.02869 | 0.1088* | |
| H11B | 0.89153 | 0.35146 | 0.01024 | 0.1088* | |
| H11C | 0.92235 | 0.71279 | 0.03486 | 0.1088* | |
| H12A | 0.82773 | 0.53290 | 0.15333 | 0.1006* | |
| H12B | 0.83789 | 0.20017 | 0.11712 | 0.1006* | |
| H12C | 0.74137 | 0.24627 | 0.15460 | 0.1006* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.064 (2) | 0.141 (3) | 0.074 (3) | 0.0185 (19) | 0.003 (2) | 0.011 (2) |
| O2 | 0.066 (3) | 0.170 (4) | 0.100 (3) | 0.011 (2) | 0.037 (2) | 0.017 (2) |
| O3 | 0.0537 (19) | 0.084 (2) | 0.051 (2) | 0.0055 (14) | 0.0022 (15) | 0.0092 (15) |
| N1 | 0.057 (3) | 0.097 (3) | 0.059 (3) | 0.002 (2) | 0.009 (2) | −0.011 (2) |
| N2 | 0.048 (2) | 0.061 (2) | 0.048 (2) | −0.0018 (17) | 0.0047 (18) | −0.0012 (16) |
| N3 | 0.065 (3) | 0.080 (3) | 0.054 (3) | −0.001 (2) | 0.011 (2) | 0.0068 (19) |
| C1 | 0.050 (3) | 0.047 (3) | 0.045 (3) | −0.0016 (19) | 0.001 (2) | −0.005 (2) |
| C2 | 0.052 (3) | 0.068 (3) | 0.053 (3) | −0.001 (2) | 0.000 (2) | −0.010 (2) |
| C3 | 0.073 (3) | 0.071 (3) | 0.045 (3) | −0.003 (2) | 0.006 (3) | −0.003 (2) |
| C4 | 0.065 (3) | 0.073 (3) | 0.049 (3) | −0.007 (2) | 0.014 (2) | −0.010 (2) |
| C5 | 0.046 (3) | 0.059 (3) | 0.054 (3) | −0.006 (2) | −0.002 (2) | −0.013 (2) |
| C6 | 0.050 (3) | 0.058 (3) | 0.045 (3) | −0.0016 (19) | 0.003 (2) | −0.005 (2) |
| C7 | 0.049 (3) | 0.065 (3) | 0.044 (3) | −0.001 (2) | 0.004 (2) | 0.000 (2) |
| C8 | 0.056 (3) | 0.056 (3) | 0.043 (3) | −0.001 (2) | −0.003 (2) | 0.003 (2) |
| C9 | 0.042 (3) | 0.055 (3) | 0.048 (3) | 0.001 (2) | 0.001 (2) | −0.003 (2) |
| C10 | 0.049 (3) | 0.053 (3) | 0.052 (3) | 0.001 (2) | 0.004 (2) | −0.005 (2) |
| C11 | 0.063 (3) | 0.079 (3) | 0.079 (4) | 0.000 (2) | 0.024 (3) | 0.000 (3) |
| C12 | 0.064 (3) | 0.078 (3) | 0.059 (3) | 0.010 (2) | 0.002 (2) | 0.002 (2) |
| O1—N1 | 1.224 (6) | C8—C9 | 1.346 (5) |
| O2—N1 | 1.217 (6) | C9—C10 | 1.400 (6) |
| O3—N3 | 1.418 (5) | C9—C12 | 1.484 (5) |
| O3—C8 | 1.362 (5) | C10—C11 | 1.498 (5) |
| N1—C5 | 1.464 (5) | C2—H2 | 0.9300 |
| N2—C7 | 1.283 (5) | C3—H3 | 0.9300 |
| N2—C8 | 1.375 (5) | C4—H4 | 0.9300 |
| N3—C10 | 1.312 (5) | C6—H6 | 0.9300 |
| C1—C2 | 1.384 (6) | C7—H7 | 0.9300 |
| C1—C6 | 1.398 (5) | C11—H11A | 0.9600 |
| C1—C7 | 1.462 (5) | C11—H11B | 0.9600 |
| C2—C3 | 1.394 (6) | C11—H11C | 0.9600 |
| C3—C4 | 1.375 (7) | C12—H12A | 0.9600 |
| C4—C5 | 1.365 (6) | C12—H12B | 0.9600 |
| C5—C6 | 1.385 (6) | C12—H12C | 0.9600 |
| N3—O3—C8 | 107.9 (3) | N3—C10—C11 | 119.2 (4) |
| O1—N1—O2 | 122.2 (4) | C9—C10—C11 | 127.9 (4) |
| O1—N1—C5 | 118.9 (4) | C1—C2—H2 | 120.00 |
| O2—N1—C5 | 118.9 (4) | C3—C2—H2 | 120.00 |
| C7—N2—C8 | 120.0 (3) | C2—C3—H3 | 120.00 |
| O3—N3—C10 | 104.8 (3) | C4—C3—H3 | 120.00 |
| C2—C1—C6 | 119.3 (4) | C3—C4—H4 | 120.00 |
| C2—C1—C7 | 121.7 (3) | C5—C4—H4 | 120.00 |
| C6—C1—C7 | 119.0 (3) | C1—C6—H6 | 121.00 |
| C1—C2—C3 | 121.0 (4) | C5—C6—H6 | 121.00 |
| C2—C3—C4 | 119.6 (4) | N2—C7—H7 | 120.00 |
| C3—C4—C5 | 119.2 (4) | C1—C7—H7 | 120.00 |
| N1—C5—C4 | 118.9 (4) | C10—C11—H11A | 109.00 |
| N1—C5—C6 | 118.2 (4) | C10—C11—H11B | 109.00 |
| C4—C5—C6 | 122.8 (4) | C10—C11—H11C | 109.00 |
| C1—C6—C5 | 118.2 (4) | H11A—C11—H11B | 109.00 |
| N2—C7—C1 | 120.1 (3) | H11A—C11—H11C | 109.00 |
| O3—C8—N2 | 120.9 (3) | H11B—C11—H11C | 109.00 |
| O3—C8—C9 | 110.1 (3) | C9—C12—H12A | 109.00 |
| N2—C8—C9 | 128.9 (4) | C9—C12—H12B | 109.00 |
| C8—C9—C10 | 104.4 (3) | C9—C12—H12C | 109.00 |
| C8—C9—C12 | 127.8 (4) | H12A—C12—H12B | 109.00 |
| C10—C9—C12 | 127.8 (3) | H12A—C12—H12C | 109.00 |
| N3—C10—C9 | 112.9 (3) | H12B—C12—H12C | 109.00 |
| C8—O3—N3—C10 | 0.2 (4) | C7—C1—C6—C5 | 179.5 (3) |
| N3—O3—C8—C9 | −0.5 (4) | C2—C1—C7—N2 | −0.9 (6) |
| N3—O3—C8—N2 | −179.4 (3) | C1—C2—C3—C4 | 1.2 (6) |
| O2—N1—C5—C4 | −0.3 (6) | C2—C3—C4—C5 | −1.4 (6) |
| O2—N1—C5—C6 | −178.9 (4) | C3—C4—C5—N1 | −177.6 (4) |
| O1—N1—C5—C4 | 179.3 (4) | C3—C4—C5—C6 | 0.9 (6) |
| O1—N1—C5—C6 | 0.7 (6) | N1—C5—C6—C1 | 178.4 (3) |
| C7—N2—C8—C9 | −179.6 (4) | C4—C5—C6—C1 | −0.2 (6) |
| C8—N2—C7—C1 | 179.4 (3) | O3—C8—C9—C10 | 0.5 (4) |
| C7—N2—C8—O3 | −0.9 (5) | N2—C8—C9—C12 | −2.5 (7) |
| O3—N3—C10—C11 | 179.1 (3) | O3—C8—C9—C12 | 178.7 (3) |
| O3—N3—C10—C9 | 0.1 (4) | N2—C8—C9—C10 | 179.4 (4) |
| C6—C1—C2—C3 | −0.4 (6) | C8—C9—C10—N3 | −0.4 (4) |
| C7—C1—C2—C3 | −180.0 (4) | C12—C9—C10—C11 | 2.5 (6) |
| C6—C1—C7—N2 | 179.6 (3) | C8—C9—C10—C11 | −179.3 (4) |
| C2—C1—C6—C5 | −0.1 (5) | C12—C9—C10—N3 | −178.6 (4) |
Experimental details
| Crystal data | |
| Chemical formula | C12H11N3O3 |
| Mr | 245.24 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 296 |
| a, b, c (Å) | 12.602 (2), 3.9267 (6), 23.366 (4) |
| β (°) | 94.791 (9) |
| V (Å3) | 1152.3 (3) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.11 |
| Crystal size (mm) | 0.22 × 0.08 × 0.06 |
| Data collection | |
| Diffractometer | Bruker Kappa APEXII CCD diffractometer |
| Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
| Tmin, Tmax | 0.992, 0.995 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 8616, 2046, 846 |
| Rint | 0.097 |
| (sin θ/λ)max (Å−1) | 0.596 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.161, 0.99 |
| No. of reflections | 2046 |
| No. of parameters | 166 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.16, −0.19 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
Acknowledgements
The authors would like to thank the Chemistry Department, King Abdul Aziz University, Jeddah, Saudi Arabia for providing research facilities and for the financial support of this work via grant No. (3–045/430).
References
Asiri, A. M., Khan, S. A. & Tahir, M. N. (2010a). Acta Cryst. E66, o2127. Web of Science CSD CrossRef IUCr Journals Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
The title compound (I, Fig. 1) is being reported in continuation of our synthetic and structural studies of various Schiff bases of 5-amino-3,4-dimethylisoxazole (Asiri et al., 2010a, b, c, d).
In (I), the 3-nitrobenzaldehyde moiety A (C1—C7/N1/O1/O2) and 5-amino-3,4-dimethylisoxazole moiety B (N2/C8—C12/N3/O3) are planar with r. m. s. deviation of 0.0124 and 0.0099 Å, respectively. The dihedral angle between A/B is 2.46 (12)°. All the heavy atoms (C1—C12/N1—N3/O1—O3) consituate plane with r. m. s. deviation of 0.0276 Å. In this plane, the methyl atom C12 deviates at the maximum with 0.0721 (33) Å. The title compound essentially consists of monomers. There exists no π···π interactions in the crystal.