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

Asiri, A.M.; Khan, S.A.; Tan, K.W.; Ng, S.W.

doi:10.1107/S1600536810026966

organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o2019

https://doi.org/10.1107/S1600536810026966

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

Abdullah M. Asiri,^a Salman A. Khan,^a Kong Wai Tan ^b and Seik Weng Ng ^b ^*

^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 ).

Experimental

Crystal data

C₁₅H₁₈N₂O₄
M_r = 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)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.139
S = 1.03
3274 reflections
195 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.33 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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810026966/bt5294Isup2.hkl

checkCIF report

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.

Structure description top

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

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

C₁₅H₁₈N₂O₄	Z = 2
M_r = 290.31	F(000) = 308
Triclinic, P1	D_x = 1.342 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6502 (5) Å	Cell parameters from 3842 reflections
b = 10.9012 (8) Å	θ = 3.1–28.3°
c = 11.2582 (8) Å	µ = 0.10 mm⁻¹
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 tube	R_int = 0.026
Graphite monochromator	θ_max = 27.5°, θ_min = 2.0°
ω scans	h = −8→7
6732 measured reflections	k = −14→14
3274 independent reflections	l = −14→14

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0858P)² + 0.1878P] where P = (F_o² + 2F_c²)/3
3274 reflections	(Δ/σ)_max = 0.001
195 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₅H₁₈N₂O₄	γ = 79.985 (1)°
M_r = 290.31	V = 718.20 (9) Å³
Triclinic, P1	Z = 2
a = 6.6502 (5) Å	Mo Kα radiation
b = 10.9012 (8) Å	µ = 0.10 mm⁻¹
c = 11.2582 (8) Å	T = 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 reflections	R_int = 0.026
3274 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.03	Δρ_max = 0.27 e Å⁻³
3274 reflections	Δρ_min = −0.33 e Å⁻³
195 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.73187 (15)	0.64886 (10)	0.40960 (10)	0.0229 (2)
O2	0.14017 (16)	0.97942 (10)	0.20733 (9)	0.0222 (2)
O3	−0.06033 (15)	0.89581 (10)	0.43158 (9)	0.0225 (2)
O4	0.72778 (15)	0.35850 (10)	0.86306 (9)	0.0212 (2)
N1	0.42768 (18)	0.50963 (11)	0.76624 (11)	0.0190 (3)
N2	0.79017 (19)	0.25984 (12)	0.99100 (11)	0.0223 (3)
C1	0.4264 (2)	0.66108 (13)	0.53406 (13)	0.0184 (3)
C2	0.5358 (2)	0.70964 (14)	0.41095 (13)	0.0185 (3)
C3	0.4429 (2)	0.81575 (14)	0.29816 (13)	0.0191 (3)
H3	0.5160	0.8470	0.2144	0.023*
C4	0.2442 (2)	0.87494 (13)	0.30920 (13)	0.0184 (3)
C5	0.1333 (2)	0.82831 (14)	0.43353 (13)	0.0187 (3)
C6	0.2246 (2)	0.72188 (14)	0.54297 (13)	0.0188 (3)
H6	0.1498	0.6889	0.6261	0.023*
C7	0.8522 (2)	0.69800 (16)	0.28703 (14)	0.0248 (3)
H7A	0.9905	0.6468	0.3013	0.037*
H7B	0.8592	0.7968	0.2555	0.037*
H7C	0.7891	0.6840	0.2205	0.037*
C8	0.2345 (2)	1.02354 (15)	0.07629 (13)	0.0215 (3)
H8A	0.1427	1.0982	0.0126	0.032*
H8B	0.2623	0.9454	0.0530	0.032*
H8C	0.3632	1.0572	0.0736	0.032*
C9	−0.1756 (2)	0.85422 (16)	0.55545 (14)	0.0246 (3)
H9A	−0.3094	0.9116	0.5426	0.037*
H9B	−0.1021	0.8657	0.6195	0.037*
H9C	−0.1944	0.7569	0.5894	0.037*
C10	0.5224 (2)	0.55118 (14)	0.65057 (13)	0.0187 (3)
H10	0.6573	0.5089	0.6419	0.022*
C11	0.5270 (2)	0.40739 (13)	0.87469 (13)	0.0182 (3)
C12	0.4552 (2)	0.34506 (13)	1.00327 (13)	0.0179 (3)
C13	0.2444 (2)	0.36953 (15)	1.05885 (14)	0.0241 (3)
H13A	0.1663	0.4497	0.9908	0.036*
H13B	0.2527	0.3874	1.1360	0.036*
H13C	0.1762	0.2876	1.0862	0.036*
C14	0.6264 (2)	0.25434 (13)	1.07118 (13)	0.0187 (3)
C15	0.6394 (2)	0.15920 (15)	1.21572 (14)	0.0242 (3)
H15A	0.7754	0.1046	1.2323	0.036*
H15B	0.5354	0.0969	1.2428	0.036*
H15C	0.6161	0.2135	1.2670	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0179 (5)	0.0253 (5)	0.0175 (5)	0.0020 (4)	0.0022 (4)	−0.0046 (4)
O2	0.0224 (5)	0.0221 (5)	0.0123 (5)	0.0029 (4)	0.0006 (4)	−0.0011 (4)
O3	0.0194 (5)	0.0247 (5)	0.0143 (5)	0.0027 (4)	0.0013 (4)	−0.0029 (4)
O4	0.0193 (5)	0.0218 (5)	0.0152 (5)	0.0017 (4)	−0.0003 (4)	−0.0033 (4)
N1	0.0199 (6)	0.0176 (5)	0.0150 (5)	−0.0004 (4)	−0.0012 (4)	−0.0039 (4)
N2	0.0238 (6)	0.0207 (6)	0.0161 (6)	0.0018 (5)	−0.0034 (5)	−0.0036 (5)
C1	0.0197 (7)	0.0176 (6)	0.0150 (6)	−0.0017 (5)	−0.0004 (5)	−0.0051 (5)
C2	0.0168 (7)	0.0190 (6)	0.0175 (6)	−0.0003 (5)	0.0004 (5)	−0.0070 (5)
C3	0.0205 (7)	0.0186 (6)	0.0145 (6)	−0.0030 (5)	0.0016 (5)	−0.0045 (5)
C4	0.0217 (7)	0.0159 (6)	0.0133 (6)	−0.0009 (5)	−0.0010 (5)	−0.0030 (5)
C5	0.0184 (7)	0.0198 (6)	0.0153 (6)	−0.0015 (5)	0.0004 (5)	−0.0059 (5)
C6	0.0202 (7)	0.0194 (6)	0.0129 (6)	−0.0024 (5)	0.0013 (5)	−0.0043 (5)
C7	0.0191 (7)	0.0323 (8)	0.0198 (7)	−0.0035 (6)	0.0055 (5)	−0.0102 (6)
C8	0.0255 (7)	0.0218 (7)	0.0116 (6)	−0.0016 (5)	0.0013 (5)	−0.0034 (5)
C9	0.0218 (7)	0.0284 (7)	0.0165 (7)	−0.0006 (6)	0.0035 (5)	−0.0058 (6)
C10	0.0185 (7)	0.0173 (6)	0.0175 (6)	−0.0001 (5)	−0.0012 (5)	−0.0059 (5)
C11	0.0176 (7)	0.0168 (6)	0.0180 (6)	0.0006 (5)	−0.0016 (5)	−0.0065 (5)
C12	0.0196 (7)	0.0157 (6)	0.0160 (6)	−0.0004 (5)	−0.0015 (5)	−0.0053 (5)
C13	0.0210 (7)	0.0262 (7)	0.0182 (7)	0.0002 (5)	0.0012 (5)	−0.0054 (6)
C14	0.0223 (7)	0.0159 (6)	0.0162 (6)	−0.0004 (5)	−0.0020 (5)	−0.0059 (5)
C15	0.0285 (8)	0.0220 (7)	0.0163 (6)	0.0015 (6)	−0.0042 (6)	−0.0042 (5)

Geometric parameters (Å, º) top

O1—C2	1.3576 (16)	C7—H7A	0.9800
O1—C7	1.4330 (16)	C7—H7B	0.9800
O2—C4	1.3570 (16)	C7—H7C	0.9800
O2—C8	1.4316 (15)	C8—H8A	0.9800
O3—C5	1.3647 (17)	C8—H8B	0.9800
O3—C9	1.4269 (16)	C8—H8C	0.9800
O4—C11	1.3623 (16)	C9—H9A	0.9800
O4—N2	1.4171 (14)	C9—H9B	0.9800
N1—C10	1.2932 (18)	C9—H9C	0.9800
N1—C11	1.3755 (17)	C10—H10	0.9500
N2—C14	1.3197 (18)	C11—C12	1.3611 (18)
C1—C6	1.403 (2)	C12—C14	1.4148 (19)
C1—C2	1.4020 (18)	C12—C13	1.4951 (19)
C1—C10	1.4474 (18)	C13—H13A	0.9800
C2—C3	1.4001 (18)	C13—H13B	0.9800
C3—C4	1.3830 (19)	C13—H13C	0.9800
C3—H3	0.9500	C14—C15	1.4919 (18)
C4—C5	1.4171 (18)	C15—H15A	0.9800
C5—C6	1.3752 (18)	C15—H15B	0.9800
C6—H6	0.9500	C15—H15C	0.9800

C2—O1—C7	118.39 (11)	O2—C8—H8C	109.5
C4—O2—C8	117.96 (10)	H8A—C8—H8C	109.5
C5—O3—C9	116.69 (10)	H8B—C8—H8C	109.5
C11—O4—N2	107.97 (10)	O3—C9—H9A	109.5
C10—N1—C11	119.06 (12)	O3—C9—H9B	109.5
C14—N2—O4	105.38 (11)	H9A—C9—H9B	109.5
C6—C1—C2	119.14 (12)	O3—C9—H9C	109.5
C6—C1—C10	120.67 (12)	H9A—C9—H9C	109.5
C2—C1—C10	120.18 (13)	H9B—C9—H9C	109.5
O1—C2—C3	123.52 (12)	N1—C10—C1	121.13 (13)
O1—C2—C1	116.28 (12)	N1—C10—H10	119.4
C3—C2—C1	120.21 (12)	C1—C10—H10	119.4
C4—C3—C2	119.75 (12)	C12—C11—O4	110.29 (11)
C4—C3—H3	120.1	C12—C11—N1	128.95 (12)
C2—C3—H3	120.1	O4—C11—N1	120.70 (12)
O2—C4—C3	124.84 (12)	C11—C12—C14	103.98 (12)
O2—C4—C5	114.60 (12)	C11—C12—C13	127.53 (12)
C3—C4—C5	120.55 (12)	C14—C12—C13	128.48 (12)
O3—C5—C6	125.95 (12)	C12—C13—H13A	109.5
O3—C5—C4	114.91 (11)	C12—C13—H13B	109.5
C6—C5—C4	119.13 (13)	H13A—C13—H13B	109.5
C5—C6—C1	121.19 (13)	C12—C13—H13C	109.5
C5—C6—H6	119.4	H13A—C13—H13C	109.5
C1—C6—H6	119.4	H13B—C13—H13C	109.5
O1—C7—H7A	109.5	N2—C14—C12	112.38 (12)
O1—C7—H7B	109.5	N2—C14—C15	119.39 (13)
H7A—C7—H7B	109.5	C12—C14—C15	128.23 (13)
O1—C7—H7C	109.5	C14—C15—H15A	109.5
H7A—C7—H7C	109.5	C14—C15—H15B	109.5
H7B—C7—H7C	109.5	H15A—C15—H15B	109.5
O2—C8—H8A	109.5	C14—C15—H15C	109.5
O2—C8—H8B	109.5	H15A—C15—H15C	109.5
H8A—C8—H8B	109.5	H15B—C15—H15C	109.5

C11—O4—N2—C14	0.25 (14)	C4—C5—C6—C1	1.4 (2)
C7—O1—C2—C3	1.6 (2)	C2—C1—C6—C5	−0.3 (2)
C7—O1—C2—C1	−178.00 (12)	C10—C1—C6—C5	178.63 (12)
C6—C1—C2—O1	178.43 (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—N1	176.54 (13)
C10—C1—C2—C3	179.87 (12)	N2—O4—C11—C12	−0.41 (15)
O1—C2—C3—C4	−177.98 (12)	N2—O4—C11—N1	177.21 (11)
C1—C2—C3—C4	1.6 (2)	C10—N1—C11—C12	−177.34 (14)
C8—O2—C4—C3	6.2 (2)	C10—N1—C11—O4	5.53 (19)
C8—O2—C4—C5	−174.26 (12)	O4—C11—C12—C14	0.40 (15)
C2—C3—C4—O2	179.01 (12)	N1—C11—C12—C14	−176.98 (13)
C2—C3—C4—C5	−0.5 (2)	O4—C11—C12—C13	179.52 (13)
C9—O3—C5—C6	1.8 (2)	N1—C11—C12—C13	2.1 (2)
C9—O3—C5—C4	−178.54 (12)	O4—N2—C14—C12	0.00 (15)
O2—C4—C5—O3	−0.17 (18)	O4—N2—C14—C15	−179.83 (11)
C3—C4—C5—O3	179.42 (12)	C11—C12—C14—N2	−0.24 (16)
O2—C4—C5—C6	179.47 (12)	C13—C12—C14—N2	−179.36 (13)
C3—C4—C5—C6	−0.9 (2)	C11—C12—C14—C15	179.57 (14)
O3—C5—C6—C1	−179.04 (13)	C13—C12—C14—C15	0.5 (2)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₈N₂O₄
M_r	290.31
Crystal system, space group	Triclinic, 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)
V (Å³)	718.20 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.35 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6732, 3274, 2660
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.139, 1.03
No. of reflections	3274
No. of parameters	195
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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

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