(E)-N-(2,3,4-Trimeth-oxy-6-methyl-benzyl-idene)aniline.

In the title compound, C(17)H(19)NO(3), the C-C=N-C torsion angle between the benzene and phenyl rings is -177.3 (2)°, and the dihedral angle between the rings is 54.6 (2)°. The crystal structure is stabilized by intra-molecular hydrogen bonds and weak π-π and C-H⋯π inter-actions.

Related literature

For related literature, see: Zhang et al. (2005 ▶).

Experimental

Crystal data

C17H19NO3

M = 285.33

Triclinic,

a = 8.3126 (13) Å

b = 9.9938 (17) Å

c = 10.8661 (19) Å

α = 110.102 (2)°

β = 111.995 (2)°

γ = 92.7000 (10)°

V = 769.8 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 298 (2) K

0.50 × 0.48 × 0.47 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.959, T max = 0.962

3966 measured reflections

2650 independent reflections

1571 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.170

S = 1.00

2650 reflections

194 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808016620/bx2141sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016620/bx2141Isup2.hkl

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

C17H19NO3	Z = 2
Mr = 285.33	F000 = 304
Triclinic, P1	Dx = 1.231 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.3126 (13) Å	Cell parameters from 1209 reflections
b = 9.9938 (17) Å	θ = 2.4–26.5º
c = 10.8661 (19) Å	µ = 0.08 mm−1
α = 110.102 (2)º	T = 298 (2) K
β = 111.995 (2)º	Block, yellow
γ = 92.7000 (10)º	0.50 × 0.48 × 0.47 mm
V = 769.8 (2) Å3

Bruker SMART CCD area-detector diffractometer	2650 independent reflections
Radiation source: fine-focus sealed tube	1571 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.034
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.2º
Absorption correction: multi-scan(SADABS; Bruker, 1997)	h = −9→9
Tmin = 0.959, Tmax = 0.962	k = −7→11
3966 measured reflections	l = −12→12

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)] = 0.053	H-atom parameters constrained
wR(F2) = 0.170	w = 1/[σ2(Fo2) + (0.0809P)2 + 0.0591P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2650 reflections	Δρmax = 0.19 e Å−3
194 parameters	Δρmin = −0.22 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
N1	0.6434 (3)	0.0882 (2)	0.7849 (2)	0.0637 (6)
O1	0.1396 (2)	0.11706 (18)	0.64766 (19)	0.0619 (5)
O2	0.0101 (2)	0.3729 (2)	0.67375 (19)	0.0642 (5)
O3	0.2329 (2)	0.62688 (18)	0.78978 (19)	0.0626 (5)
C1	0.4895 (3)	0.1089 (3)	0.7390 (3)	0.0489 (6)
H1	0.3988	0.0268	0.6846	0.059*
C2	0.4379 (3)	0.2505 (2)	0.7625 (2)	0.0424 (6)
C3	0.2546 (3)	0.2493 (2)	0.7129 (2)	0.0457 (6)
C4	0.1898 (3)	0.3749 (3)	0.7225 (2)	0.0468 (6)
C5	0.3079 (3)	0.5078 (3)	0.7853 (2)	0.0471 (6)
C6	0.4884 (3)	0.5112 (3)	0.8370 (2)	0.0470 (6)
H6	0.5664	0.6004	0.8804	0.056*
C7	0.5564 (3)	0.3853 (3)	0.8261 (2)	0.0452 (6)
C8	0.0442 (5)	0.0901 (4)	0.7236 (4)	0.0963 (11)
H8A	0.1254	0.0873	0.8125	0.144*
H8B	−0.0376	−0.0015	0.6660	0.144*
H8C	−0.0198	0.1663	0.7438	0.144*
C9	−0.0840 (4)	0.3143 (4)	0.5226 (3)	0.0889 (11)
H9A	−0.0245	0.3586	0.4815	0.133*
H9B	−0.2018	0.3333	0.4977	0.133*
H9C	−0.0900	0.2112	0.4858	0.133*
C10	0.3479 (4)	0.7643 (3)	0.8476 (3)	0.0751 (9)
H10A	0.4278	0.7854	0.9456	0.113*
H10B	0.2790	0.8385	0.8448	0.113*
H10C	0.4144	0.7616	0.7915	0.113*
C11	0.7545 (3)	0.4004 (3)	0.8838 (3)	0.0616 (7)
H11A	0.8096	0.5015	0.9259	0.092*
H11B	0.7866	0.3496	0.8066	0.092*
H11C	0.7936	0.3599	0.9558	0.092*
C12	0.6728 (3)	−0.0566 (3)	0.7476 (3)	0.0504 (6)
C13	0.7910 (3)	−0.0901 (3)	0.8552 (3)	0.0649 (8)
H13	0.8417	−0.0205	0.9492	0.078*
C14	0.8357 (4)	−0.2241 (3)	0.8266 (4)	0.0736 (8)
H14	0.9156	−0.2451	0.9009	0.088*
C15	0.7636 (5)	−0.3261 (3)	0.6901 (4)	0.0758 (9)
H15	0.7945	−0.4169	0.6708	0.091*
C16	0.6450 (4)	−0.2958 (3)	0.5803 (3)	0.0746 (9)
H16	0.5953	−0.3660	0.4867	0.090*
C17	0.5994 (4)	−0.1610 (3)	0.6089 (3)	0.0614 (7)
H17	0.5190	−0.1404	0.5345	0.074*

	U11	U22	U33	U12	U13	U23
N1	0.0507 (14)	0.0530 (14)	0.0845 (16)	0.0168 (11)	0.0250 (12)	0.0260 (12)
O1	0.0464 (10)	0.0564 (11)	0.0774 (13)	0.0030 (8)	0.0300 (9)	0.0160 (9)
O2	0.0420 (10)	0.0785 (13)	0.0730 (13)	0.0211 (9)	0.0266 (9)	0.0264 (10)
O3	0.0661 (12)	0.0558 (11)	0.0766 (12)	0.0272 (9)	0.0343 (10)	0.0311 (9)
C1	0.0447 (15)	0.0542 (15)	0.0534 (14)	0.0107 (12)	0.0250 (12)	0.0224 (12)
C2	0.0423 (13)	0.0477 (14)	0.0424 (13)	0.0130 (11)	0.0208 (11)	0.0194 (10)
C3	0.0430 (14)	0.0489 (15)	0.0461 (13)	0.0089 (11)	0.0227 (11)	0.0150 (11)
C4	0.0398 (14)	0.0578 (16)	0.0471 (14)	0.0158 (12)	0.0220 (11)	0.0202 (11)
C5	0.0522 (15)	0.0507 (15)	0.0475 (14)	0.0196 (12)	0.0266 (12)	0.0219 (11)
C6	0.0465 (14)	0.0481 (14)	0.0461 (13)	0.0063 (11)	0.0197 (11)	0.0181 (11)
C7	0.0427 (14)	0.0535 (15)	0.0458 (13)	0.0130 (12)	0.0214 (11)	0.0230 (11)
C8	0.110 (3)	0.081 (2)	0.134 (3)	0.0123 (19)	0.084 (3)	0.046 (2)
C9	0.0557 (18)	0.108 (3)	0.075 (2)	0.0228 (18)	0.0085 (16)	0.0230 (19)
C10	0.094 (2)	0.0561 (18)	0.080 (2)	0.0248 (16)	0.0366 (18)	0.0302 (15)
C11	0.0456 (15)	0.0611 (17)	0.0775 (18)	0.0098 (12)	0.0219 (14)	0.0304 (14)
C12	0.0419 (14)	0.0499 (15)	0.0683 (17)	0.0136 (11)	0.0293 (13)	0.0256 (13)
C13	0.0525 (16)	0.0590 (17)	0.0702 (18)	0.0132 (13)	0.0153 (14)	0.0215 (14)
C14	0.0603 (18)	0.071 (2)	0.094 (2)	0.0209 (15)	0.0252 (17)	0.0437 (18)
C15	0.094 (2)	0.0582 (19)	0.104 (3)	0.0350 (17)	0.061 (2)	0.0383 (18)
C16	0.099 (2)	0.0641 (19)	0.0689 (19)	0.0214 (17)	0.0485 (18)	0.0202 (15)
C17	0.0710 (18)	0.0653 (18)	0.0662 (18)	0.0230 (14)	0.0393 (15)	0.0334 (15)

N1—C1	1.244 (3)	C9—H9A	0.9600
N1—C12	1.422 (3)	C9—H9B	0.9600
O1—C3	1.376 (3)	C9—H9C	0.9600
O1—C8	1.416 (3)	C10—H10A	0.9600
O2—C4	1.382 (3)	C10—H10B	0.9600
O2—C9	1.409 (3)	C10—H10C	0.9600
O3—C5	1.363 (3)	C11—H11A	0.9600
O3—C10	1.423 (3)	C11—H11B	0.9600
C1—C2	1.464 (3)	C11—H11C	0.9600
C1—H1	0.9300	C12—C13	1.373 (4)
C2—C7	1.410 (3)	C12—C17	1.379 (4)
C2—C3	1.411 (3)	C13—C14	1.370 (4)
C3—C4	1.375 (3)	C13—H13	0.9300
C4—C5	1.396 (3)	C14—C15	1.355 (4)
C5—C6	1.385 (3)	C14—H14	0.9300
C6—C7	1.389 (3)	C15—C16	1.372 (4)
C6—H6	0.9300	C15—H15	0.9300
C7—C11	1.505 (3)	C16—C17	1.380 (4)
C8—H8A	0.9600	C16—H16	0.9300
C8—H8B	0.9600	C17—H17	0.9300
C8—H8C	0.9600
C1—N1—C12	119.4 (2)	O2—C9—H9C	109.5
C3—O1—C8	116.2 (2)	H9A—C9—H9C	109.5
C4—O2—C9	114.82 (19)	H9B—C9—H9C	109.5
C5—O3—C10	117.8 (2)	O3—C10—H10A	109.5
N1—C1—C2	126.0 (2)	O3—C10—H10B	109.5
N1—C1—H1	117.0	H10A—C10—H10B	109.5
C2—C1—H1	117.0	O3—C10—H10C	109.5
C7—C2—C3	118.4 (2)	H10A—C10—H10C	109.5
C7—C2—C1	125.0 (2)	H10B—C10—H10C	109.5
C3—C2—C1	116.5 (2)	C7—C11—H11A	109.5
C4—C3—O1	120.0 (2)	C7—C11—H11B	109.5
C4—C3—C2	121.8 (2)	H11A—C11—H11B	109.5
O1—C3—C2	118.1 (2)	C7—C11—H11C	109.5
C3—C4—O2	121.5 (2)	H11A—C11—H11C	109.5
C3—C4—C5	119.4 (2)	H11B—C11—H11C	109.5
O2—C4—C5	119.1 (2)	C13—C12—C17	118.6 (2)
O3—C5—C6	124.8 (2)	C13—C12—N1	117.4 (2)
O3—C5—C4	115.7 (2)	C17—C12—N1	123.8 (2)
C6—C5—C4	119.5 (2)	C14—C13—C12	121.1 (3)
C5—C6—C7	122.0 (2)	C14—C13—H13	119.4
C5—C6—H6	119.0	C12—C13—H13	119.4
C7—C6—H6	119.0	C15—C14—C13	120.0 (3)
C6—C7—C2	118.9 (2)	C15—C14—H14	120.0
C6—C7—C11	117.9 (2)	C13—C14—H14	120.0
C2—C7—C11	123.2 (2)	C14—C15—C16	120.2 (3)
O1—C8—H8A	109.5	C14—C15—H15	119.9
O1—C8—H8B	109.5	C16—C15—H15	119.9
H8A—C8—H8B	109.5	C15—C16—C17	119.9 (3)
O1—C8—H8C	109.5	C15—C16—H16	120.0
H8A—C8—H8C	109.5	C17—C16—H16	120.0
H8B—C8—H8C	109.5	C12—C17—C16	120.1 (3)
O2—C9—H9A	109.5	C12—C17—H17	119.9
O2—C9—H9B	109.5	C16—C17—H17	119.9
H9A—C9—H9B	109.5
C12—N1—C1—C2	−177.3 (2)	O2—C4—C5—C6	178.8 (2)
N1—C1—C2—C7	8.3 (4)	O3—C5—C6—C7	−178.4 (2)
N1—C1—C2—C3	−173.8 (2)	C4—C5—C6—C7	1.2 (3)
C8—O1—C3—C4	−70.8 (3)	C5—C6—C7—C2	−1.1 (3)
C8—O1—C3—C2	112.1 (3)	C5—C6—C7—C11	179.2 (2)
C7—C2—C3—C4	1.3 (3)	C3—C2—C7—C6	−0.2 (3)
C1—C2—C3—C4	−176.7 (2)	C1—C2—C7—C6	177.7 (2)
C7—C2—C3—O1	178.33 (19)	C3—C2—C7—C11	179.6 (2)
C1—C2—C3—O1	0.3 (3)	C1—C2—C7—C11	−2.6 (4)
O1—C3—C4—O2	3.0 (3)	C1—N1—C12—C13	−136.1 (3)
C2—C3—C4—O2	−180.0 (2)	C1—N1—C12—C17	48.6 (4)
O1—C3—C4—C5	−178.2 (2)	C17—C12—C13—C14	−0.1 (4)
C2—C3—C4—C5	−1.2 (3)	N1—C12—C13—C14	−175.7 (2)
C9—O2—C4—C3	−72.5 (3)	C12—C13—C14—C15	0.3 (4)
C9—O2—C4—C5	108.7 (3)	C13—C14—C15—C16	−0.3 (5)
C10—O3—C5—C6	2.1 (3)	C14—C15—C16—C17	0.2 (4)
C10—O3—C5—C4	−177.6 (2)	C13—C12—C17—C16	0.0 (4)
C3—C4—C5—O3	179.6 (2)	N1—C12—C17—C16	175.2 (2)
O2—C4—C5—O3	−1.6 (3)	C15—C16—C17—C12	0.0 (4)
C3—C4—C5—C6	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1	0.93	2.32	2.714 (3)	105
C8—H8C···O2	0.96	2.47	3.062 (5)	120
C9—H9C···O1	0.96	2.53	3.079 (4)	116
C10—H10C···Cg2i	0.96	2.98	3.894 (4)	160

CgI-CgJ	CgI···CgJ	Dihedral angle	Interplanar distance	Offset
Cg1-Cg1i	4.236 (1)	0	3.523 (1)	2.352

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the ring C12–C17.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1	0.93	2.32	2.714 (3)	105
C8—H8C⋯O2	0.96	2.47	3.062 (5)	120
C9—H9C⋯O1	0.96	2.53	3.079 (4)	116
C10—H10C⋯Cg2i	0.96	2.98	3.894 (4)	160

Symmetry code: (i) .

Table 2

π–π interactions (Å, °)

Cg1 is the centroid of the ring C2–C7. The offset is defined as the distance between CgI and the perpendicular projection of CgJ on ring I.

CgI⋯CgJ	CgI⋯CgJ	Dihedral angle	Interplanar distance	Offset
Cg1⋯Cg1i	4.236 (1)		3.523 (1)	2.352

Symmetry code: (i) .