

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810023780/jh2170sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810023780/jh2170Isup2.hkl |
CCDC reference: 786698
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(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
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.
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.
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).
![]() | Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C14H13N3O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. |
C14H17N3O | Z = 2 |
Mr = 243.31 | F(000) = 260 |
Triclinic, P1 | Dx = 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 |
Bruker SMART APEX diffractometer | 2401 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 27.5°, θmin = 1.9° |
ω scans | h = −8→8 |
6092 measured reflections | k = −11→11 |
2866 independent reflections | l = −13→13 |
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(Fo2) + (0.0652P)2 + 0.0819P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
2866 reflections | Δρmax = 0.25 e Å−3 |
168 parameters | Δρmin = −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) |
C14H17N3O | γ = 90.873 (1)° |
Mr = 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)° |
Bruker SMART APEX diffractometer | 2401 reflections with I > 2σ(I) |
6092 measured reflections | Rint = 0.023 |
2866 independent reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.25 e Å−3 |
2866 reflections | Δρmin = −0.24 e Å−3 |
168 parameters |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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 |
Mr | 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 |
Rint | 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 |
Δρmax, Δρmin (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).
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) °].