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organic compounds Acta Crystallographica Section E b = 3.9267 (6) Å c = 23.366 (4) Å = 94.791 (9) V = 1152.3 (3) Å3 Z=4 Structure Reports Online ISSN 1600-5368 Mo K radiation  = 0.11 mm 1 T = 296 K 0.22  0.08  0.06 mm Data collection 3,4-Dimethyl-N-[(E)-3-nitrobenzylidene]1,2-oxazol-5-amine Abdullah M. Asiri,a,b Salman A. Khanb and M. Nawaz Tahirc* a The 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 Received 5 September 2010; accepted 6 September 2010 Key indicators: single-crystal X-ray study; T = 296 K; mean (C–C) = 0.006 Å; R factor = 0.061; wR factor = 0.161; data-to-parameter ratio = 12.3. In the title compound, C12H11N3O3, the dihedral angle between the 3-nitrobenzaldehyde and 5-amino-3,4-dimethyl1,2-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. For background and related crystal structures, see: Asiri et al. (2010a,b,c,d). Experimental Crystal data Acta Cryst. (2010). E66, o2539 8616 measured reflections 2046 independent reflections 846 reflections with I > 2(I) Rint = 0.097 Refinement R[F 2 > 2(F 2)] = 0.061 wR(F 2) = 0.161 S = 0.99 2046 reflections 166 parameters H-atom parameters constrained
max = 0.16 e Å 3
min = 0.19 e Å 3 Data collection: APEX2 (Bruker, 2009); cell refinement: 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. 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). Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5634). Related literature C12H11N3O3 Mr = 245.24 Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005) Tmin = 0.992, Tmax = 0.995 Monoclinic, P21 =c a = 12.602 (2) Å References Asiri, A. M., Khan, S. A. & Tahir, M. N. (2010a). Acta Cryst. E66, o2127. Asiri, A. M., Khan, S. A. & Tahir, M. N. (2010b). Acta Cryst. E66, o2077. Asiri, A. M., Khan, S. A., Tan, K. W. & Ng, S. W. (2010c). Acta Cryst. E66, o2046. Asiri, A. M., Khan, S. A., Tan, K. W. & Ng, S. W. (2010d). Acta Cryst. E66, o2019. Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Spek, A. L. (2009). Acta Cryst. D65, 148–155. doi:10.1107/S160053681003583X Asiri et al. o2539 supplementary materials supplementary materials Acta Cryst. (2010). E66, o2539 [ doi:10.1107/S160053681003583X ] 3,4-Dimethyl-N-[(E)-3-nitrobenzylidene]-1,2-oxazol-5-amine A. M. Asiri, S. A. Khan and M. N. Tahir Comment 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. Experimental 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). Refinement 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. Figures Fig. 1. View of (I) with displacement ellipsoids drawn at the 50% probability level. 3,4-Dimethyl-N-[(E)-3-nitrobenzylidene]-1,2-oxazol-5-amine Crystal data C12H11N3O3 F(000) = 512 Mr = 245.24 Dx = 1.414 Mg m−3 sup-1 supplementary materials Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å Hall symbol: -P 2ybc a = 12.602 (2) Å Cell parameters from 846 reflections θ = 2.3–25.0° b = 3.9267 (6) Å µ = 0.11 mm−1 T = 296 K Needle, colorless c = 23.366 (4) Å β = 94.791 (9)° V = 1152.3 (3) Å3 Z=4 0.22 × 0.08 × 0.06 mm Data collection Bruker Kappa APEXII CCD diffractometer Radiation source: fine-focus sealed tube graphite Detector resolution: 8.20 pixels mm-1 ω scans Absorption correction: multi-scan (SADABS; Bruker, 2005) Tmin = 0.992, Tmax = 0.995 2046 independent reflections 846 reflections with I > 2σ(I) Rint = 0.097 θmax = 25.0°, θmin = 2.3° h = −15→15 k = −4→4 l = −27→27 8616 measured reflections Refinement R[F2 > 2σ(F2)] = 0.061 Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites wR(F2) = 0.161 H-atom parameters constrained Refinement on F2 Least-squares matrix: full 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 Special details 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 Rfactors(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. sup-2 supplementary materials Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) O1 O2 O3 N1 N2 N3 C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 H2 H3 H4 H6 H7 H11A H11B H11C H12A H12B H12C x y z Uiso*/Ueq 0.0661 (2) 0.0217 (3) 0.5961 (2) 0.0873 (3) 0.5490 (3) 0.6882 (3) 0.3736 (3) 0.3985 (3) 0.3218 (4) 0.2194 (4) 0.1954 (3) 0.2697 (3) 0.4530 (3) 0.6232 (3) 0.7266 (3) 0.7629 (3) 0.8723 (3) 0.7889 (3) 0.46743 0.33974 0.16713 0.25095 0.43386 0.87321 0.89153 0.92235 0.82773 0.83789 0.74137 0.9618 (9) 0.7756 (9) 0.7628 (6) 0.8153 (10) 0.5694 (8) 0.7702 (8) 0.6218 (9) 0.4605 (10) 0.4146 (10) 0.5255 (10) 0.6856 (10) 0.7379 (9) 0.6720 (9) 0.6142 (10) 0.5238 (9) 0.6275 (9) 0.5881 (10) 0.3614 (10) 0.38159 0.30952 0.49195 0.84733 0.77846 0.67477 0.35146 0.71279 0.53290 0.20017 0.24627 0.11316 (16) 0.19373 (16) 0.02581 (12) 0.15894 (19) 0.11691 (13) −0.00509 (15) 0.14659 (17) 0.19866 (18) 0.23763 (18) 0.22380 (19) 0.17248 (19) 0.13294 (17) 0.10518 (17) 0.07766 (17) 0.08165 (17) 0.02938 (19) 0.00968 (19) 0.13104 (17) 0.20778 0.27277 0.24908 0.09826 0.07029 −0.02869 0.01024 0.03486 0.15333 0.11712 0.15460 0.0932 (16) 0.1103 (19) 0.0630 (11) 0.0708 (17) 0.0523 (12) 0.0660 (17) 0.0475 (17) 0.0579 (17) 0.0629 (17) 0.0618 (17) 0.0534 (17) 0.0511 (17) 0.0527 (17) 0.0521 (17) 0.0485 (17) 0.0513 (17) 0.0727 (19) 0.0672 (17) 0.0695* 0.0758* 0.0742* 0.0611* 0.0629* 0.1088* 0.1088* 0.1088* 0.1006* 0.1006* 0.1006* Atomic displacement parameters (Å2) O1 O2 O3 N1 N2 N3 C1 C2 C3 C4 C5 U11 0.064 (2) 0.066 (3) 0.0537 (19) 0.057 (3) 0.048 (2) 0.065 (3) 0.050 (3) 0.052 (3) 0.073 (3) 0.065 (3) 0.046 (3) U22 0.141 (3) 0.170 (4) 0.084 (2) 0.097 (3) 0.061 (2) 0.080 (3) 0.047 (3) 0.068 (3) 0.071 (3) 0.073 (3) 0.059 (3) U33 0.074 (3) 0.100 (3) 0.051 (2) 0.059 (3) 0.048 (2) 0.054 (3) 0.045 (3) 0.053 (3) 0.045 (3) 0.049 (3) 0.054 (3) U12 0.0185 (19) 0.011 (2) 0.0055 (14) 0.002 (2) −0.0018 (17) −0.001 (2) −0.0016 (19) −0.001 (2) −0.003 (2) −0.007 (2) −0.006 (2) U13 0.003 (2) 0.037 (2) 0.0022 (15) 0.009 (2) 0.0047 (18) 0.011 (2) 0.001 (2) 0.000 (2) 0.006 (3) 0.014 (2) −0.002 (2) U23 0.011 (2) 0.017 (2) 0.0092 (15) −0.011 (2) −0.0012 (16) 0.0068 (19) −0.005 (2) −0.010 (2) −0.003 (2) −0.010 (2) −0.013 (2) sup-3 supplementary materials C6 C7 C8 C9 C10 C11 C12 0.050 (3) 0.049 (3) 0.056 (3) 0.042 (3) 0.049 (3) 0.063 (3) 0.064 (3) 0.058 (3) 0.065 (3) 0.056 (3) 0.055 (3) 0.053 (3) 0.079 (3) 0.078 (3) 0.045 (3) 0.044 (3) 0.043 (3) 0.048 (3) 0.052 (3) 0.079 (4) 0.059 (3) −0.0016 (19) −0.001 (2) −0.001 (2) 0.001 (2) 0.001 (2) 0.000 (2) 0.010 (2) 0.003 (2) 0.004 (2) −0.003 (2) 0.001 (2) 0.004 (2) 0.024 (3) 0.002 (2) −0.005 (2) 0.000 (2) 0.003 (2) −0.003 (2) −0.005 (2) 0.000 (3) 0.002 (2) Geometric parameters (Å, °) O1—N1 O2—N1 O3—N3 O3—C8 N1—C5 N2—C7 N2—C8 N3—C10 C1—C2 C1—C6 C1—C7 C2—C3 C3—C4 C4—C5 C5—C6 1.224 (6) 1.217 (6) 1.418 (5) 1.362 (5) 1.464 (5) 1.283 (5) 1.375 (5) 1.312 (5) 1.384 (6) 1.398 (5) 1.462 (5) 1.394 (6) 1.375 (7) 1.365 (6) 1.385 (6) C8—C9 C9—C10 C9—C12 C10—C11 C2—H2 C3—H3 C4—H4 C6—H6 C7—H7 C11—H11A C11—H11B C11—H11C C12—H12A C12—H12B C12—H12C 1.346 (5) 1.400 (6) 1.484 (5) 1.498 (5) 0.9300 0.9300 0.9300 0.9300 0.9300 0.9600 0.9600 0.9600 0.9600 0.9600 0.9600 N3—O3—C8 O1—N1—O2 O1—N1—C5 O2—N1—C5 C7—N2—C8 O3—N3—C10 C2—C1—C6 C2—C1—C7 C6—C1—C7 C1—C2—C3 C2—C3—C4 C3—C4—C5 N1—C5—C4 N1—C5—C6 C4—C5—C6 C1—C6—C5 N2—C7—C1 O3—C8—N2 O3—C8—C9 N2—C8—C9 C8—C9—C10 C8—C9—C12 C10—C9—C12 N3—C10—C9 107.9 (3) 122.2 (4) 118.9 (4) 118.9 (4) 120.0 (3) 104.8 (3) 119.3 (4) 121.7 (3) 119.0 (3) 121.0 (4) 119.6 (4) 119.2 (4) 118.9 (4) 118.2 (4) 122.8 (4) 118.2 (4) 120.1 (3) 120.9 (3) 110.1 (3) 128.9 (4) 104.4 (3) 127.8 (4) 127.8 (3) 112.9 (3) N3—C10—C11 C9—C10—C11 C1—C2—H2 C3—C2—H2 C2—C3—H3 C4—C3—H3 C3—C4—H4 C5—C4—H4 C1—C6—H6 C5—C6—H6 N2—C7—H7 C1—C7—H7 C10—C11—H11A C10—C11—H11B C10—C11—H11C H11A—C11—H11B H11A—C11—H11C H11B—C11—H11C C9—C12—H12A C9—C12—H12B C9—C12—H12C H12A—C12—H12B H12A—C12—H12C H12B—C12—H12C 119.2 (4) 127.9 (4) 120.00 120.00 120.00 120.00 120.00 120.00 121.00 121.00 120.00 120.00 109.00 109.00 109.00 109.00 109.00 109.00 109.00 109.00 109.00 109.00 109.00 109.00 sup-4 supplementary materials C8—O3—N3—C10 N3—O3—C8—C9 N3—O3—C8—N2 O2—N1—C5—C4 O2—N1—C5—C6 O1—N1—C5—C4 O1—N1—C5—C6 C7—N2—C8—C9 C8—N2—C7—C1 C7—N2—C8—O3 O3—N3—C10—C11 O3—N3—C10—C9 C6—C1—C2—C3 C7—C1—C2—C3 C6—C1—C7—N2 C2—C1—C6—C5 0.2 (4) −0.5 (4) −179.4 (3) −0.3 (6) −178.9 (4) 179.3 (4) 0.7 (6) −179.6 (4) 179.4 (3) −0.9 (5) 179.1 (3) 0.1 (4) −0.4 (6) −180.0 (4) 179.6 (3) −0.1 (5) C7—C1—C6—C5 C2—C1—C7—N2 C1—C2—C3—C4 C2—C3—C4—C5 C3—C4—C5—N1 C3—C4—C5—C6 N1—C5—C6—C1 C4—C5—C6—C1 O3—C8—C9—C10 N2—C8—C9—C12 O3—C8—C9—C12 N2—C8—C9—C10 C8—C9—C10—N3 C12—C9—C10—C11 C8—C9—C10—C11 C12—C9—C10—N3 179.5 (3) −0.9 (6) 1.2 (6) −1.4 (6) −177.6 (4) 0.9 (6) 178.4 (3) −0.2 (6) 0.5 (4) −2.5 (7) 178.7 (3) 179.4 (4) −0.4 (4) 2.5 (6) −179.3 (4) −178.6 (4) sup-5 supplementary materials Fig. 1 sup-6