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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)°].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810023780/jh2170sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536810023780/jh2170Isup2.hkl
Contains datablock I

CCDC reference: 786698

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.039
  • wR factor = 0.113
  • Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 9 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 8
Alert level G PLAT154_ALERT_1_G The su's on the Cell Angles are Equal (x 10000) 100 Deg.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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–CN–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.

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.

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. 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
C14H17N3OZ = 2
Mr = 243.31F(000) = 260
Triclinic, P1Dx = 1.285 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.5772 (6) ÅCell parameters from 2610 reflections
b = 9.1246 (9) Åθ = 2.2–28.3°
c = 10.538 (1) ŵ = 0.08 mm1
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 tubeRint = 0.023
Graphite monochromatorθmax = 27.5°, θmin = 1.9°
ω scansh = 88
6092 measured reflectionsk = 1111
2866 independent reflectionsl = 1313
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.113 w = 1/[σ2(Fo2) + (0.0652P)2 + 0.0819P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
2866 reflectionsΔρmax = 0.25 e Å3
168 parametersΔρmin = 0.24 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.024 (5)
Crystal data top
C14H17N3Oγ = 90.873 (1)°
Mr = 243.31V = 628.86 (10) Å3
Triclinic, P1Z = 2
a = 6.5772 (6) ÅMo Kα radiation
b = 9.1246 (9) ŵ = 0.08 mm1
c = 10.538 (1) ÅT = 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 reflectionsRint = 0.023
2866 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.113H-atom parameters constrained
S = 1.04Δρmax = 0.25 e Å3
2866 reflectionsΔρmin = 0.24 e Å3
168 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.34307 (12)0.64426 (8)0.20359 (7)0.0212 (2)
N20.46514 (14)0.43648 (10)0.31374 (9)0.0188 (2)
N30.41200 (15)0.73832 (10)0.11248 (9)0.0229 (2)
N10.13966 (15)0.02064 (10)0.73244 (9)0.0214 (2)
C10.06808 (18)0.00795 (14)0.76262 (12)0.0275 (3)
H1A0.12580.08310.79590.041*
H1B0.06730.08160.82710.041*
H1C0.15110.04460.68520.041*
C30.17610 (17)0.11519 (11)0.64040 (10)0.0175 (2)
C20.29986 (19)0.07284 (12)0.78465 (12)0.0251 (3)
H2A0.32700.14990.72040.038*
H2B0.25610.11790.86040.038*
H2C0.42450.01380.80840.038*
C40.37269 (17)0.13022 (12)0.59705 (10)0.0189 (2)
H40.47970.06990.62930.023*
C50.41094 (17)0.23055 (12)0.50920 (10)0.0184 (2)
H50.54470.23910.48270.022*
C60.25736 (16)0.32079 (12)0.45762 (10)0.0176 (2)
C70.06149 (17)0.30343 (12)0.49799 (11)0.0194 (2)
H70.04570.36220.46340.023*
C80.01988 (17)0.20356 (12)0.58643 (11)0.0201 (2)
H80.11480.19410.61130.024*
C90.29510 (17)0.42739 (12)0.36576 (10)0.0185 (2)
H90.19030.49390.34240.022*
C100.49005 (17)0.54187 (12)0.22757 (10)0.0180 (2)
C110.64745 (16)0.56405 (11)0.15557 (10)0.0180 (2)
C120.83736 (17)0.47749 (13)0.14888 (11)0.0237 (3)
H12A0.84860.40970.21820.036*
H12B0.95640.54440.15740.036*
H12C0.83180.42150.06670.036*
C130.58994 (17)0.68813 (12)0.08652 (10)0.0197 (2)
C140.71023 (19)0.76199 (13)0.00676 (11)0.0245 (3)
H14A0.71540.69720.08350.037*
H14B0.84930.78330.03200.037*
H14C0.64480.85380.02990.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0190 (4)0.0238 (4)0.0218 (4)0.0006 (3)0.0047 (3)0.0072 (3)
N20.0200 (5)0.0196 (5)0.0168 (5)0.0031 (4)0.0033 (4)0.0010 (3)
N30.0236 (5)0.0256 (5)0.0203 (5)0.0034 (4)0.0033 (4)0.0088 (4)
N10.0200 (5)0.0231 (5)0.0224 (5)0.0003 (4)0.0047 (4)0.0078 (4)
C10.0240 (6)0.0296 (6)0.0311 (7)0.0021 (5)0.0093 (5)0.0117 (5)
C30.0197 (6)0.0169 (5)0.0160 (5)0.0017 (4)0.0026 (4)0.0006 (4)
C20.0285 (6)0.0216 (6)0.0267 (6)0.0039 (5)0.0053 (5)0.0092 (5)
C40.0176 (5)0.0198 (5)0.0193 (5)0.0015 (4)0.0022 (4)0.0015 (4)
C50.0157 (5)0.0208 (5)0.0190 (5)0.0020 (4)0.0039 (4)0.0001 (4)
C60.0179 (5)0.0188 (5)0.0159 (5)0.0020 (4)0.0018 (4)0.0001 (4)
C70.0165 (5)0.0224 (5)0.0197 (5)0.0010 (4)0.0015 (4)0.0034 (4)
C80.0160 (5)0.0241 (6)0.0207 (6)0.0013 (4)0.0038 (4)0.0026 (4)
C90.0173 (5)0.0211 (5)0.0168 (5)0.0012 (4)0.0007 (4)0.0012 (4)
C100.0182 (5)0.0189 (5)0.0165 (5)0.0020 (4)0.0000 (4)0.0003 (4)
C110.0184 (5)0.0206 (5)0.0146 (5)0.0047 (4)0.0010 (4)0.0004 (4)
C120.0197 (6)0.0280 (6)0.0242 (6)0.0016 (4)0.0045 (5)0.0038 (5)
C130.0205 (6)0.0227 (5)0.0156 (5)0.0052 (4)0.0003 (4)0.0006 (4)
C140.0267 (6)0.0273 (6)0.0201 (6)0.0054 (5)0.0039 (5)0.0046 (5)
Geometric parameters (Å, º) top
O1—C101.3709 (13)C5—C61.4025 (15)
O1—N31.4201 (11)C5—H50.9500
N2—C91.2926 (14)C6—C71.4020 (15)
N2—C101.3745 (14)C6—C91.4419 (15)
N3—C131.3097 (15)C7—C81.3788 (15)
N1—C31.3659 (14)C7—H70.9500
N1—C21.4533 (14)C8—H80.9500
N1—C11.4534 (14)C9—H90.9500
C1—H1A0.9800C10—C111.3565 (15)
C1—H1B0.9800C11—C131.4155 (15)
C1—H1C0.9800C11—C121.4930 (15)
C3—C81.4132 (15)C12—H12A0.9800
C3—C41.4168 (15)C12—H12B0.9800
C2—H2A0.9800C12—H12C0.9800
C2—H2B0.9800C13—C141.4966 (15)
C2—H2C0.9800C14—H14A0.9800
C4—C51.3718 (15)C14—H14B0.9800
C4—H40.9500C14—H14C0.9800
C10—O1—N3107.86 (8)C8—C7—C6121.91 (10)
C9—N2—C10119.52 (10)C8—C7—H7119.0
C13—N3—O1105.28 (9)C6—C7—H7119.0
C3—N1—C2120.76 (9)C7—C8—C3120.48 (10)
C3—N1—C1120.12 (9)C7—C8—H8119.8
C2—N1—C1118.15 (9)C3—C8—H8119.8
N1—C1—H1A109.5N2—C9—C6122.97 (10)
N1—C1—H1B109.5N2—C9—H9118.5
H1A—C1—H1B109.5C6—C9—H9118.5
N1—C1—H1C109.5C11—C10—O1109.95 (10)
H1A—C1—H1C109.5C11—C10—N2129.32 (10)
H1B—C1—H1C109.5O1—C10—N2120.73 (9)
N1—C3—C8121.22 (10)C10—C11—C13104.10 (10)
N1—C3—C4121.27 (10)C10—C11—C12128.36 (10)
C8—C3—C4117.50 (10)C13—C11—C12127.54 (10)
N1—C2—H2A109.5C11—C12—H12A109.5
N1—C2—H2B109.5C11—C12—H12B109.5
H2A—C2—H2B109.5H12A—C12—H12B109.5
N1—C2—H2C109.5C11—C12—H12C109.5
H2A—C2—H2C109.5H12A—C12—H12C109.5
H2B—C2—H2C109.5H12B—C12—H12C109.5
C5—C4—C3121.04 (10)N3—C13—C11112.81 (10)
C5—C4—H4119.5N3—C13—C14120.31 (10)
C3—C4—H4119.5C11—C13—C14126.88 (11)
C4—C5—C6121.58 (10)C13—C14—H14A109.5
C4—C5—H5119.2C13—C14—H14B109.5
C6—C5—H5119.2H14A—C14—H14B109.5
C7—C6—C5117.44 (10)C13—C14—H14C109.5
C7—C6—C9120.23 (10)H14A—C14—H14C109.5
C5—C6—C9122.33 (10)H14B—C14—H14C109.5
C10—O1—N3—C130.59 (11)C7—C6—C9—N2171.57 (10)
C2—N1—C3—C8178.20 (10)C5—C6—C9—N27.97 (17)
C1—N1—C3—C89.66 (16)N3—O1—C10—C110.86 (11)
C2—N1—C3—C42.91 (16)N3—O1—C10—N2179.38 (9)
C1—N1—C3—C4171.45 (10)C9—N2—C10—C11174.71 (11)
N1—C3—C4—C5176.74 (10)C9—N2—C10—O15.00 (15)
C8—C3—C4—C52.19 (16)O1—C10—C11—C130.75 (12)
C3—C4—C5—C60.80 (17)N2—C10—C11—C13179.51 (10)
C4—C5—C6—C70.81 (16)O1—C10—C11—C12178.70 (10)
C4—C5—C6—C9179.64 (9)N2—C10—C11—C121.03 (19)
C5—C6—C7—C81.00 (16)O1—N3—C13—C110.13 (12)
C9—C6—C7—C8179.45 (10)O1—N3—C13—C14179.61 (9)
C6—C7—C8—C30.44 (17)C10—C11—C13—N30.38 (13)
N1—C3—C8—C7176.93 (10)C12—C11—C13—N3179.08 (10)
C4—C3—C8—C72.01 (16)C10—C11—C13—C14179.06 (10)
C10—N2—C9—C6179.54 (9)C12—C11—C13—C141.47 (18)

Experimental details

Crystal data
Chemical formulaC14H17N3O
Mr243.31
Crystal system, space groupTriclinic, 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)
V3)628.86 (10)
Z2
Radiation typeMo Kα
µ (mm1)0.08
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
6092, 2866, 2401
Rint0.023
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.113, 1.04
No. of reflections2866
No. of parameters168
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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).

 

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