N-[4-(Dimethyl-amino)-benzyl-idene]-3,4-dimethyl-isoxazol-5-amine.

The aromatic rings attached to the azomethine double bond in the title compound, C(14)H(17)N(3)O, 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 = 243.31

Triclinic,

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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.113

S = 1.04

2866 reflections

168 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023780/jh2170sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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	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)

	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)