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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o2019.
Published online 2010 July 14. doi:  10.1107/S1600536810026966
PMCID: PMC3007490

3,4-Dimethyl-N-(2,4,5-trimeth­oxy­benzyl­idene)-1,2-isoxazol-5-amine

Abstract

In the title compound, C15H18N2O4, the aromatic rings on the azomethine double bond are trans to each other [C—C=N—C torsion angle = −178.29 (12)°] and they are approximately coplanar, the dihedral angle between them being 5.0 (1)°.

Related literature

For the spectroscopic characterization of a related Schiff base, see: Asiri et al. (2010 [triangle]).

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Object name is e-66-o2019-scheme1.jpg

Experimental

Crystal data

  • C15H18N2O4
  • M r = 290.31
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2019-efi1.jpg
  • a = 6.6502 (5) Å
  • b = 10.9012 (8) Å
  • c = 11.2582 (8) Å
  • α = 63.463 (1)°
  • β = 83.078 (1)°
  • γ = 79.985 (1)°
  • V = 718.20 (9) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 100 K
  • 0.35 × 0.15 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • 6732 measured reflections
  • 3274 independent reflections
  • 2660 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.139
  • S = 1.03
  • 3274 reflections
  • 195 parameters
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810026966/bt5294sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026966/bt5294Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank King Abdul Aziz University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The is yet no structural report on a Schiff-base condensation product involving 5-amino-3,4-dimethylisoxazole, a commerically available chemical. We recently reported the spectroscopic characterization of the N-ethylcarbazole-3-aldehyde condensation product of this amine (Asiri et al., 2010). The 2,4,5-trimethyoxybenzaldehyde condensation product (Scheme I, Fig. 1) features an azomethine double-bond whose aromatic substituents are located in trans positions. The rings are coplanar [dihedral angle 5.0 (1)°].

Experimental

5-Amino-3,4-dimethylisoxazole (0.36 g, 3.2 mol) and 2,4,5-trimethoxybenzaldehyde (0.62 g, 3.2 mol) were heated in methanol (15 ml) for 5 h. The solvent was removed and the solid material recrystallized from methanol to give the crystalline Schiff base.

Refinement

Carbon-bound H-atoms were placed in calculated positions [C–H 0.95 to 0.98 Å, U(H) 1.2 to 1.5Ueq(C)] and were included in the refinement in the riding model approximation.

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of C15H18N2O4 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C15H18N2O4Z = 2
Mr = 290.31F(000) = 308
Triclinic, P1Dx = 1.342 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.6502 (5) ÅCell parameters from 3842 reflections
b = 10.9012 (8) Åθ = 3.1–28.3°
c = 11.2582 (8) ŵ = 0.10 mm1
α = 63.463 (1)°T = 100 K
β = 83.078 (1)°Prism, yellow
γ = 79.985 (1)°0.35 × 0.15 × 0.10 mm
V = 718.20 (9) Å3

Data collection

Bruker SMART APEX diffractometer2660 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
graphiteθmax = 27.5°, θmin = 2.0°
ω scansh = −8→7
6732 measured reflectionsk = −14→14
3274 independent reflectionsl = −14→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0858P)2 + 0.1878P] where P = (Fo2 + 2Fc2)/3
3274 reflections(Δ/σ)max = 0.001
195 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = −0.33 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.73187 (15)0.64886 (10)0.40960 (10)0.0229 (2)
O20.14017 (16)0.97942 (10)0.20733 (9)0.0222 (2)
O3−0.06033 (15)0.89581 (10)0.43158 (9)0.0225 (2)
O40.72778 (15)0.35850 (10)0.86306 (9)0.0212 (2)
N10.42768 (18)0.50963 (11)0.76624 (11)0.0190 (3)
N20.79017 (19)0.25984 (12)0.99100 (11)0.0223 (3)
C10.4264 (2)0.66108 (13)0.53406 (13)0.0184 (3)
C20.5358 (2)0.70964 (14)0.41095 (13)0.0185 (3)
C30.4429 (2)0.81575 (14)0.29816 (13)0.0191 (3)
H30.51600.84700.21440.023*
C40.2442 (2)0.87494 (13)0.30920 (13)0.0184 (3)
C50.1333 (2)0.82831 (14)0.43353 (13)0.0187 (3)
C60.2246 (2)0.72188 (14)0.54297 (13)0.0188 (3)
H60.14980.68890.62610.023*
C70.8522 (2)0.69800 (16)0.28703 (14)0.0248 (3)
H7A0.99050.64680.30130.037*
H7B0.85920.79680.25550.037*
H7C0.78910.68400.22050.037*
C80.2345 (2)1.02354 (15)0.07629 (13)0.0215 (3)
H8A0.14271.09820.01260.032*
H8B0.26230.94540.05300.032*
H8C0.36321.05720.07360.032*
C9−0.1756 (2)0.85422 (16)0.55545 (14)0.0246 (3)
H9A−0.30940.91160.54260.037*
H9B−0.10210.86570.61950.037*
H9C−0.19440.75690.58940.037*
C100.5224 (2)0.55118 (14)0.65057 (13)0.0187 (3)
H100.65730.50890.64190.022*
C110.5270 (2)0.40739 (13)0.87469 (13)0.0182 (3)
C120.4552 (2)0.34506 (13)1.00327 (13)0.0179 (3)
C130.2444 (2)0.36953 (15)1.05885 (14)0.0241 (3)
H13A0.16630.44970.99080.036*
H13B0.25270.38741.13600.036*
H13C0.17620.28761.08620.036*
C140.6264 (2)0.25434 (13)1.07118 (13)0.0187 (3)
C150.6394 (2)0.15920 (15)1.21572 (14)0.0242 (3)
H15A0.77540.10461.23230.036*
H15B0.53540.09691.24280.036*
H15C0.61610.21351.26700.036*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0179 (5)0.0253 (5)0.0175 (5)0.0020 (4)0.0022 (4)−0.0046 (4)
O20.0224 (5)0.0221 (5)0.0123 (5)0.0029 (4)0.0006 (4)−0.0011 (4)
O30.0194 (5)0.0247 (5)0.0143 (5)0.0027 (4)0.0013 (4)−0.0029 (4)
O40.0193 (5)0.0218 (5)0.0152 (5)0.0017 (4)−0.0003 (4)−0.0033 (4)
N10.0199 (6)0.0176 (5)0.0150 (5)−0.0004 (4)−0.0012 (4)−0.0039 (4)
N20.0238 (6)0.0207 (6)0.0161 (6)0.0018 (5)−0.0034 (5)−0.0036 (5)
C10.0197 (7)0.0176 (6)0.0150 (6)−0.0017 (5)−0.0004 (5)−0.0051 (5)
C20.0168 (7)0.0190 (6)0.0175 (6)−0.0003 (5)0.0004 (5)−0.0070 (5)
C30.0205 (7)0.0186 (6)0.0145 (6)−0.0030 (5)0.0016 (5)−0.0045 (5)
C40.0217 (7)0.0159 (6)0.0133 (6)−0.0009 (5)−0.0010 (5)−0.0030 (5)
C50.0184 (7)0.0198 (6)0.0153 (6)−0.0015 (5)0.0004 (5)−0.0059 (5)
C60.0202 (7)0.0194 (6)0.0129 (6)−0.0024 (5)0.0013 (5)−0.0043 (5)
C70.0191 (7)0.0323 (8)0.0198 (7)−0.0035 (6)0.0055 (5)−0.0102 (6)
C80.0255 (7)0.0218 (7)0.0116 (6)−0.0016 (5)0.0013 (5)−0.0034 (5)
C90.0218 (7)0.0284 (7)0.0165 (7)−0.0006 (6)0.0035 (5)−0.0058 (6)
C100.0185 (7)0.0173 (6)0.0175 (6)−0.0001 (5)−0.0012 (5)−0.0059 (5)
C110.0176 (7)0.0168 (6)0.0180 (6)0.0006 (5)−0.0016 (5)−0.0065 (5)
C120.0196 (7)0.0157 (6)0.0160 (6)−0.0004 (5)−0.0015 (5)−0.0053 (5)
C130.0210 (7)0.0262 (7)0.0182 (7)0.0002 (5)0.0012 (5)−0.0054 (6)
C140.0223 (7)0.0159 (6)0.0162 (6)−0.0004 (5)−0.0020 (5)−0.0059 (5)
C150.0285 (8)0.0220 (7)0.0163 (6)0.0015 (6)−0.0042 (6)−0.0042 (5)

Geometric parameters (Å, °)

O1—C21.3576 (16)C7—H7A0.9800
O1—C71.4330 (16)C7—H7B0.9800
O2—C41.3570 (16)C7—H7C0.9800
O2—C81.4316 (15)C8—H8A0.9800
O3—C51.3647 (17)C8—H8B0.9800
O3—C91.4269 (16)C8—H8C0.9800
O4—C111.3623 (16)C9—H9A0.9800
O4—N21.4171 (14)C9—H9B0.9800
N1—C101.2932 (18)C9—H9C0.9800
N1—C111.3755 (17)C10—H100.9500
N2—C141.3197 (18)C11—C121.3611 (18)
C1—C61.403 (2)C12—C141.4148 (19)
C1—C21.4020 (18)C12—C131.4951 (19)
C1—C101.4474 (18)C13—H13A0.9800
C2—C31.4001 (18)C13—H13B0.9800
C3—C41.3830 (19)C13—H13C0.9800
C3—H30.9500C14—C151.4919 (18)
C4—C51.4171 (18)C15—H15A0.9800
C5—C61.3752 (18)C15—H15B0.9800
C6—H60.9500C15—H15C0.9800
C2—O1—C7118.39 (11)O2—C8—H8C109.5
C4—O2—C8117.96 (10)H8A—C8—H8C109.5
C5—O3—C9116.69 (10)H8B—C8—H8C109.5
C11—O4—N2107.97 (10)O3—C9—H9A109.5
C10—N1—C11119.06 (12)O3—C9—H9B109.5
C14—N2—O4105.38 (11)H9A—C9—H9B109.5
C6—C1—C2119.14 (12)O3—C9—H9C109.5
C6—C1—C10120.67 (12)H9A—C9—H9C109.5
C2—C1—C10120.18 (13)H9B—C9—H9C109.5
O1—C2—C3123.52 (12)N1—C10—C1121.13 (13)
O1—C2—C1116.28 (12)N1—C10—H10119.4
C3—C2—C1120.21 (12)C1—C10—H10119.4
C4—C3—C2119.75 (12)C12—C11—O4110.29 (11)
C4—C3—H3120.1C12—C11—N1128.95 (12)
C2—C3—H3120.1O4—C11—N1120.70 (12)
O2—C4—C3124.84 (12)C11—C12—C14103.98 (12)
O2—C4—C5114.60 (12)C11—C12—C13127.53 (12)
C3—C4—C5120.55 (12)C14—C12—C13128.48 (12)
O3—C5—C6125.95 (12)C12—C13—H13A109.5
O3—C5—C4114.91 (11)C12—C13—H13B109.5
C6—C5—C4119.13 (13)H13A—C13—H13B109.5
C5—C6—C1121.19 (13)C12—C13—H13C109.5
C5—C6—H6119.4H13A—C13—H13C109.5
C1—C6—H6119.4H13B—C13—H13C109.5
O1—C7—H7A109.5N2—C14—C12112.38 (12)
O1—C7—H7B109.5N2—C14—C15119.39 (13)
H7A—C7—H7B109.5C12—C14—C15128.23 (13)
O1—C7—H7C109.5C14—C15—H15A109.5
H7A—C7—H7C109.5C14—C15—H15B109.5
H7B—C7—H7C109.5H15A—C15—H15B109.5
O2—C8—H8A109.5C14—C15—H15C109.5
O2—C8—H8B109.5H15A—C15—H15C109.5
H8A—C8—H8B109.5H15B—C15—H15C109.5
C11—O4—N2—C140.25 (14)C4—C5—C6—C11.4 (2)
C7—O1—C2—C31.6 (2)C2—C1—C6—C5−0.3 (2)
C7—O1—C2—C1−178.00 (12)C10—C1—C6—C5178.63 (12)
C6—C1—C2—O1178.43 (12)C11—N1—C10—C1−178.29 (12)
C10—C1—C2—O1−0.54 (19)C6—C1—C10—N1−2.4 (2)
C6—C1—C2—C3−1.2 (2)C2—C1—C10—N1176.54 (13)
C10—C1—C2—C3179.87 (12)N2—O4—C11—C12−0.41 (15)
O1—C2—C3—C4−177.98 (12)N2—O4—C11—N1177.21 (11)
C1—C2—C3—C41.6 (2)C10—N1—C11—C12−177.34 (14)
C8—O2—C4—C36.2 (2)C10—N1—C11—O45.53 (19)
C8—O2—C4—C5−174.26 (12)O4—C11—C12—C140.40 (15)
C2—C3—C4—O2179.01 (12)N1—C11—C12—C14−176.98 (13)
C2—C3—C4—C5−0.5 (2)O4—C11—C12—C13179.52 (13)
C9—O3—C5—C61.8 (2)N1—C11—C12—C132.1 (2)
C9—O3—C5—C4−178.54 (12)O4—N2—C14—C120.00 (15)
O2—C4—C5—O3−0.17 (18)O4—N2—C14—C15−179.83 (11)
C3—C4—C5—O3179.42 (12)C11—C12—C14—N2−0.24 (16)
O2—C4—C5—C6179.47 (12)C13—C12—C14—N2−179.36 (13)
C3—C4—C5—C6−0.9 (2)C11—C12—C14—C15179.57 (14)
O3—C5—C6—C1−179.04 (13)C13—C12—C14—C150.5 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5294).

References

  • Asiri, A. M., Khan, S. A. & Rasul, M. G. (2010). Molbank, M684
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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