organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

aChemistry Department, Faculty of Science, King Abdul Aziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 7 July 2010; accepted 7 July 2010; online 14 July 2010)

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[Asiri, A. M., Khan, S. A. & Rasul, M. G. (2010). Molbank, M684.]).

[Scheme 1]

Experimental

Crystal data
  • C15H18N2O4

  • Mr = 290.31

  • Triclinic, [P \overline 1]

  • 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)

  • Rint = 0.026

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 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[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

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)°].

Related literature top

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

Experimental top

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 top

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.

Structure description top

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)°].

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

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: 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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C15H18N2O4 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
3,4-Dimethyl-N-(2,4,5-trimethoxybenzylidene)-1,2-isoxazol-5-amine top
Crystal data top
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 top
Bruker SMART APEX
diffractometer
2660 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 27.5°, θmin = 2.0°
ω scansh = 87
6732 measured reflectionsk = 1414
3274 independent reflectionsl = 1414
Refinement top
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 = 1.03 w = 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
Crystal data top
C15H18N2O4γ = 79.985 (1)°
Mr = 290.31V = 718.20 (9) Å3
Triclinic, P1Z = 2
a = 6.6502 (5) ÅMo Kα radiation
b = 10.9012 (8) ŵ = 0.10 mm1
c = 11.2582 (8) ÅT = 100 K
α = 63.463 (1)°0.35 × 0.15 × 0.10 mm
β = 83.078 (1)°
Data collection top
Bruker SMART APEX
diffractometer
2660 reflections with I > 2σ(I)
6732 measured reflectionsRint = 0.026
3274 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.139H-atom parameters constrained
S = 1.03Δρmax = 0.27 e Å3
3274 reflectionsΔρmin = 0.33 e Å3
195 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
O30.06033 (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*
C90.1756 (2)0.85422 (16)0.55545 (14)0.0246 (3)
H9A0.30940.91160.54260.037*
H9B0.10210.86570.61950.037*
H9C0.19440.75690.58940.037*
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) top
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, º) top
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—C50.3 (2)
C7—O1—C2—C1178.00 (12)C10—C1—C6—C5178.63 (12)
C6—C1—C2—O1178.43 (12)C11—N1—C10—C1178.29 (12)
C10—C1—C2—O10.54 (19)C6—C1—C10—N12.4 (2)
C6—C1—C2—C31.2 (2)C2—C1—C10—N1176.54 (13)
C10—C1—C2—C3179.87 (12)N2—O4—C11—C120.41 (15)
O1—C2—C3—C4177.98 (12)N2—O4—C11—N1177.21 (11)
C1—C2—C3—C41.6 (2)C10—N1—C11—C12177.34 (14)
C8—O2—C4—C36.2 (2)C10—N1—C11—O45.53 (19)
C8—O2—C4—C5174.26 (12)O4—C11—C12—C140.40 (15)
C2—C3—C4—O2179.01 (12)N1—C11—C12—C14176.98 (13)
C2—C3—C4—C50.5 (2)O4—C11—C12—C13179.52 (13)
C9—O3—C5—C61.8 (2)N1—C11—C12—C132.1 (2)
C9—O3—C5—C4178.54 (12)O4—N2—C14—C120.00 (15)
O2—C4—C5—O30.17 (18)O4—N2—C14—C15179.83 (11)
C3—C4—C5—O3179.42 (12)C11—C12—C14—N20.24 (16)
O2—C4—C5—C6179.47 (12)C13—C12—C14—N2179.36 (13)
C3—C4—C5—C60.9 (2)C11—C12—C14—C15179.57 (14)
O3—C5—C6—C1179.04 (13)C13—C12—C14—C150.5 (2)

Experimental details

Crystal data
Chemical formulaC15H18N2O4
Mr290.31
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)6.6502 (5), 10.9012 (8), 11.2582 (8)
α, β, γ (°)63.463 (1), 83.078 (1), 79.985 (1)
V3)718.20 (9)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.35 × 0.15 × 0.10
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6732, 3274, 2660
Rint0.026
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.139, 1.03
No. of reflections3274
No. of parameters195
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.33

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

 

Acknowledgements

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

References

First citationAsiri, A. M., Khan, S. A. & Rasul, M. G. (2010). Molbank, M684CrossRef Google Scholar
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
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