3,4-Dimethyl-N-(2,4,5-trimeth-oxy-benzyl-idene)-1,2-isoxazol-5-amine.

In the title compound, C(15)H(18)N(2)O(4), 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 = 290.31

Triclinic,

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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.139

S = 1.03

3274 reflections

195 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −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 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026966/bt5294Isup2.hkl

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

C15H18N2O4	Z = 2
Mr = 290.31	F(000) = 308
Triclinic, P1	Dx = 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

Bruker SMART APEX diffractometer	2660 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
graphite	θmax = 27.5°, θmin = 2.0°
ω scans	h = −8→7
6732 measured reflections	k = −14→14
3274 independent reflections	l = −14→14

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(Fo2) + (0.0858P)2 + 0.1878P] where P = (Fo2 + 2Fc2)/3
3274 reflections	(Δ/σ)max = 0.001
195 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)