N-[4-(Dimethyl­amino)­benzyl­idene]-3,4-dimethyl­isoxazol-5-amine

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

doi:10.1107/S1600536810023780

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1783

doi:10.1107/S1600536810023780

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N-[4-(Dimethylamino)benzylidene]-3,4-dimethylisoxazol-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 15 June 2010; accepted 19 June 2010; online 26 June 2010)

The aromatic rings attached to the azomethine double bond in the title compound, C₁₄H₁₇N₃O, are trans to each other [C—C=N—C torsion angle = 179.5 (1)°], and they are approximately coplanar [dihedral angle between the five- and six-membered rings = 13.7 (1)°].

Related literature

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

Experimental

Crystal data

C₁₄H₁₇N₃O
M_r = 243.31
Triclinic, $[P \overline 1]$
a = 6.5772 (6) Å
b = 9.1246 (9) Å
c = 10.538 (1) Å
α = 92.995 (1)°
β = 95.183 (1)°
γ = 90.873 (1)°
V = 628.86 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.35 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
6092 measured reflections
2866 independent reflections
2401 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.113
S = 1.04
2866 reflections
168 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.24 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: 10.1107/S1600536810023780/jh2170sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810023780/jh2170Isup2.hkl

checkCIF report

Comment top

Although there is a large number of crystal structure studies of Schiff bases derived by condensing an aromatic aldehyde and an aromatic amine, there has not been any structural report on the condensation product involving 5-amino-3,4-dimethylisoxazole, a commerically available chemical. We have recently reported the spectroscopic characterization of the N-ethylcarbazole-3-aldehyde condensation product of this amine (Asiri et al., 2010). The 4-dimethylaminobenzaldehyde condensation product (Scheme I, Fig. 1) features an azomethine double-bond whose aromatic substituents are located in trans positions. The rings are coplanar [C–C═N–C torsion angle 179.5 (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 N,N-dimethylaminobenzaldehyde (0.5 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.

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. Thermal ellipsoid plot (Barbour, 2001) of C₁₄H₁₃N₃O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

N-[4-(Dimethylamino)benzylidene]-3,4-dimethylisoxazol-5-amine top

Crystal data top

C₁₄H₁₇N₃O	Z = 2
M_r = 243.31	F(000) = 260
Triclinic, P1	D_x = 1.285 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5772 (6) Å	Cell parameters from 2610 reflections
b = 9.1246 (9) Å	θ = 2.2–28.3°
c = 10.538 (1) Å	µ = 0.08 mm⁻¹
α = 92.995 (1)°	T = 100 K
β = 95.183 (1)°	Prism, yellow
γ = 90.873 (1)°	0.35 × 0.15 × 0.10 mm
V = 628.86 (10) Å³

Data collection top

Bruker SMART APEX diffractometer	2401 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 27.5°, θ_min = 1.9°
ω scans	h = −8→8
6092 measured reflections	k = −11→11
2866 independent reflections	l = −13→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.113	w = 1/[σ²(F_o²) + (0.0652P)² + 0.0819P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
2866 reflections	Δρ_max = 0.25 e Å⁻³
168 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (5)

Crystal data top

C₁₄H₁₇N₃O	γ = 90.873 (1)°
M_r = 243.31	V = 628.86 (10) Å³
Triclinic, P1	Z = 2
a = 6.5772 (6) Å	Mo Kα radiation
b = 9.1246 (9) Å	µ = 0.08 mm⁻¹
c = 10.538 (1) Å	T = 100 K
α = 92.995 (1)°	0.35 × 0.15 × 0.10 mm
β = 95.183 (1)°

Data collection top

Bruker SMART APEX diffractometer	2401 reflections with I > 2σ(I)
6092 measured reflections	R_int = 0.023
2866 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.04	Δρ_max = 0.25 e Å⁻³
2866 reflections	Δρ_min = −0.24 e Å⁻³
168 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.34307 (12)	0.64426 (8)	0.20359 (7)	0.0212 (2)
N2	0.46514 (14)	0.43648 (10)	0.31374 (9)	0.0188 (2)
N3	0.41200 (15)	0.73832 (10)	0.11248 (9)	0.0229 (2)
N1	0.13966 (15)	0.02064 (10)	0.73244 (9)	0.0214 (2)
C1	−0.06808 (18)	−0.00795 (14)	0.76262 (12)	0.0275 (3)
H1A	−0.1258	0.0831	0.7959	0.041*
H1B	−0.0673	−0.0816	0.8271	0.041*
H1C	−0.1511	−0.0446	0.6852	0.041*
C3	0.17610 (17)	0.11519 (11)	0.64040 (10)	0.0175 (2)
C2	0.29986 (19)	−0.07284 (12)	0.78465 (12)	0.0251 (3)
H2A	0.3270	−0.1499	0.7204	0.038*
H2B	0.2561	−0.1179	0.8604	0.038*
H2C	0.4245	−0.0138	0.8084	0.038*
C4	0.37269 (17)	0.13022 (12)	0.59705 (10)	0.0189 (2)
H4	0.4797	0.0699	0.6293	0.023*
C5	0.41094 (17)	0.23055 (12)	0.50920 (10)	0.0184 (2)
H5	0.5447	0.2391	0.4827	0.022*
C6	0.25736 (16)	0.32079 (12)	0.45762 (10)	0.0176 (2)
C7	0.06149 (17)	0.30343 (12)	0.49799 (11)	0.0194 (2)
H7	−0.0457	0.3622	0.4634	0.023*
C8	0.01988 (17)	0.20356 (12)	0.58643 (11)	0.0201 (2)
H8	−0.1148	0.1941	0.6113	0.024*
C9	0.29510 (17)	0.42739 (12)	0.36576 (10)	0.0185 (2)
H9	0.1903	0.4939	0.3424	0.022*
C10	0.49005 (17)	0.54187 (12)	0.22757 (10)	0.0180 (2)
C11	0.64745 (16)	0.56405 (11)	0.15557 (10)	0.0180 (2)
C12	0.83736 (17)	0.47749 (13)	0.14888 (11)	0.0237 (3)
H12A	0.8486	0.4097	0.2182	0.036*
H12B	0.9564	0.5444	0.1574	0.036*
H12C	0.8318	0.4215	0.0667	0.036*
C13	0.58994 (17)	0.68813 (12)	0.08652 (10)	0.0197 (2)
C14	0.71023 (19)	0.76199 (13)	−0.00676 (11)	0.0245 (3)
H14A	0.7154	0.6972	−0.0835	0.037*
H14B	0.8493	0.7833	0.0320	0.037*
H14C	0.6448	0.8538	−0.0299	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0190 (4)	0.0238 (4)	0.0218 (4)	−0.0006 (3)	0.0047 (3)	0.0072 (3)
N2	0.0200 (5)	0.0196 (5)	0.0168 (5)	−0.0031 (4)	0.0033 (4)	0.0010 (3)
N3	0.0236 (5)	0.0256 (5)	0.0203 (5)	−0.0034 (4)	0.0033 (4)	0.0088 (4)
N1	0.0200 (5)	0.0231 (5)	0.0224 (5)	−0.0003 (4)	0.0047 (4)	0.0078 (4)
C1	0.0240 (6)	0.0296 (6)	0.0311 (7)	−0.0021 (5)	0.0093 (5)	0.0117 (5)
C3	0.0197 (6)	0.0169 (5)	0.0160 (5)	−0.0017 (4)	0.0026 (4)	0.0006 (4)
C2	0.0285 (6)	0.0216 (6)	0.0267 (6)	0.0039 (5)	0.0053 (5)	0.0092 (5)
C4	0.0176 (5)	0.0198 (5)	0.0193 (5)	0.0015 (4)	0.0022 (4)	0.0015 (4)
C5	0.0157 (5)	0.0208 (5)	0.0190 (5)	−0.0020 (4)	0.0039 (4)	−0.0001 (4)
C6	0.0179 (5)	0.0188 (5)	0.0159 (5)	−0.0020 (4)	0.0018 (4)	0.0001 (4)
C7	0.0165 (5)	0.0224 (5)	0.0197 (5)	0.0010 (4)	0.0015 (4)	0.0034 (4)
C8	0.0160 (5)	0.0241 (6)	0.0207 (6)	−0.0013 (4)	0.0038 (4)	0.0026 (4)
C9	0.0173 (5)	0.0211 (5)	0.0168 (5)	−0.0012 (4)	0.0007 (4)	0.0012 (4)
C10	0.0182 (5)	0.0189 (5)	0.0165 (5)	−0.0020 (4)	0.0000 (4)	0.0003 (4)
C11	0.0184 (5)	0.0206 (5)	0.0146 (5)	−0.0047 (4)	0.0010 (4)	0.0004 (4)
C12	0.0197 (6)	0.0280 (6)	0.0242 (6)	−0.0016 (4)	0.0045 (5)	0.0038 (5)
C13	0.0205 (6)	0.0227 (5)	0.0156 (5)	−0.0052 (4)	0.0003 (4)	0.0006 (4)
C14	0.0267 (6)	0.0273 (6)	0.0201 (6)	−0.0054 (5)	0.0039 (5)	0.0046 (5)

Geometric parameters (Å, º) top

O1—C10	1.3709 (13)	C5—C6	1.4025 (15)
O1—N3	1.4201 (11)	C5—H5	0.9500
N2—C9	1.2926 (14)	C6—C7	1.4020 (15)
N2—C10	1.3745 (14)	C6—C9	1.4419 (15)
N3—C13	1.3097 (15)	C7—C8	1.3788 (15)
N1—C3	1.3659 (14)	C7—H7	0.9500
N1—C2	1.4533 (14)	C8—H8	0.9500
N1—C1	1.4534 (14)	C9—H9	0.9500
C1—H1A	0.9800	C10—C11	1.3565 (15)
C1—H1B	0.9800	C11—C13	1.4155 (15)
C1—H1C	0.9800	C11—C12	1.4930 (15)
C3—C8	1.4132 (15)	C12—H12A	0.9800
C3—C4	1.4168 (15)	C12—H12B	0.9800
C2—H2A	0.9800	C12—H12C	0.9800
C2—H2B	0.9800	C13—C14	1.4966 (15)
C2—H2C	0.9800	C14—H14A	0.9800
C4—C5	1.3718 (15)	C14—H14B	0.9800
C4—H4	0.9500	C14—H14C	0.9800

C10—O1—N3	107.86 (8)	C8—C7—C6	121.91 (10)
C9—N2—C10	119.52 (10)	C8—C7—H7	119.0
C13—N3—O1	105.28 (9)	C6—C7—H7	119.0
C3—N1—C2	120.76 (9)	C7—C8—C3	120.48 (10)
C3—N1—C1	120.12 (9)	C7—C8—H8	119.8
C2—N1—C1	118.15 (9)	C3—C8—H8	119.8
N1—C1—H1A	109.5	N2—C9—C6	122.97 (10)
N1—C1—H1B	109.5	N2—C9—H9	118.5
H1A—C1—H1B	109.5	C6—C9—H9	118.5
N1—C1—H1C	109.5	C11—C10—O1	109.95 (10)
H1A—C1—H1C	109.5	C11—C10—N2	129.32 (10)
H1B—C1—H1C	109.5	O1—C10—N2	120.73 (9)
N1—C3—C8	121.22 (10)	C10—C11—C13	104.10 (10)
N1—C3—C4	121.27 (10)	C10—C11—C12	128.36 (10)
C8—C3—C4	117.50 (10)	C13—C11—C12	127.54 (10)
N1—C2—H2A	109.5	C11—C12—H12A	109.5
N1—C2—H2B	109.5	C11—C12—H12B	109.5
H2A—C2—H2B	109.5	H12A—C12—H12B	109.5
N1—C2—H2C	109.5	C11—C12—H12C	109.5
H2A—C2—H2C	109.5	H12A—C12—H12C	109.5
H2B—C2—H2C	109.5	H12B—C12—H12C	109.5
C5—C4—C3	121.04 (10)	N3—C13—C11	112.81 (10)
C5—C4—H4	119.5	N3—C13—C14	120.31 (10)
C3—C4—H4	119.5	C11—C13—C14	126.88 (11)
C4—C5—C6	121.58 (10)	C13—C14—H14A	109.5
C4—C5—H5	119.2	C13—C14—H14B	109.5
C6—C5—H5	119.2	H14A—C14—H14B	109.5
C7—C6—C5	117.44 (10)	C13—C14—H14C	109.5
C7—C6—C9	120.23 (10)	H14A—C14—H14C	109.5
C5—C6—C9	122.33 (10)	H14B—C14—H14C	109.5

C10—O1—N3—C13	0.59 (11)	C7—C6—C9—N2	−171.57 (10)
C2—N1—C3—C8	178.20 (10)	C5—C6—C9—N2	7.97 (17)
C1—N1—C3—C8	9.66 (16)	N3—O1—C10—C11	−0.86 (11)
C2—N1—C3—C4	−2.91 (16)	N3—O1—C10—N2	179.38 (9)
C1—N1—C3—C4	−171.45 (10)	C9—N2—C10—C11	−174.71 (11)
N1—C3—C4—C5	−176.74 (10)	C9—N2—C10—O1	5.00 (15)
C8—C3—C4—C5	2.19 (16)	O1—C10—C11—C13	0.75 (12)
C3—C4—C5—C6	−0.80 (17)	N2—C10—C11—C13	−179.51 (10)
C4—C5—C6—C7	−0.81 (16)	O1—C10—C11—C12	−178.70 (10)
C4—C5—C6—C9	179.64 (9)	N2—C10—C11—C12	1.03 (19)
C5—C6—C7—C8	1.00 (16)	O1—N3—C13—C11	−0.13 (12)
C9—C6—C7—C8	−179.45 (10)	O1—N3—C13—C14	−179.61 (9)
C6—C7—C8—C3	0.44 (17)	C10—C11—C13—N3	−0.38 (13)
N1—C3—C8—C7	176.93 (10)	C12—C11—C13—N3	179.08 (10)
C4—C3—C8—C7	−2.01 (16)	C10—C11—C13—C14	179.06 (10)
C10—N2—C9—C6	−179.54 (9)	C12—C11—C13—C14	−1.47 (18)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₇N₃O
M_r	243.31
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	6.5772 (6), 9.1246 (9), 10.538 (1)
α, β, γ (°)	92.995 (1), 95.183 (1), 90.873 (1)
V (Å³)	628.86 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
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	6092, 2866, 2401
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.113, 1.04
No. of reflections	2866
No. of parameters	168
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.24

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

Asiri, A. M., Khan, S. A. & Rasul, M. G. (2010). Molbank, M684, 3 pp. Google Scholar
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Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted. Google Scholar