(E)-4-Methyl-N-(2,3,4-trimeth­oxy-6-methyl­benzyl­idene)aniline

Wang, C.-Y.

doi:10.1107/S1600536809004115

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o493

doi:10.1107/S1600536809004115

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(E)-4-Methyl-N-(2,3,4-trimethoxy-6-methylbenzylidene)aniline

Cheng-Yun Wang ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: wcywfu@163.com

(Received 1 February 2009; accepted 4 February 2009; online 11 February 2009)

In the title molecule, C₁₈H₂₁NO₃, the dihedral angle between the two benzene rings is 42.2 (2)° and it adopts a trans configuration with respect to the central C=N bond.

Related literature

For the structure of the related compound (E)-N-(2,3,4-trimethoxy-6-methylbenzylidene)naphthalen-1-amine, see: Wang (2009 ).

Experimental

Crystal data

C₁₈H₂₁NO₃
M_r = 299.36
Monoclinic, P 2₁ /c
a = 7.7239 (9) Å
b = 27.287 (2) Å
c = 8.4128 (11) Å
β = 111.529 (2)°
V = 1649.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.45 × 0.43 × 0.40 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.964, T_max = 0.968
8258 measured reflections
2899 independent reflections
1475 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.150
S = 1.02
2899 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.18 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004115/lh2770sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809004115/lh2770Isup2.hkl

checkCIF report

Comment top

The preparation, properties and applications of Schiff bases are important in the development of coordination chemistry. In this paper, the structure of the title compound, (I), is reported. The molecular structure of (I) is illustrated in Fig. 1. The bond lengths and angles of the title compound agree with those in the related compound (E)-N-(2,3,4-trimethoxy-6-methylbenzylidene)naphthalen-1-amine (Wang, 2009), as representative example. The dihedral angle between between the two phenyl rings is 137.8 (2) °. The molecule adopts a trans configuration about the central C=N functional bond. In the crystal structure, molecules pack in a 'herring-bone' fashion along the b axis direction (see fig. 2).

Related literature top

For the structure of the related compound (E)-N-(2,3,4-trimethoxy-6-methylbenzylidene)naphthalen-1-amine, see: Wang (2009).

Experimental top

A mixture of p-toluidine (0.535 g, 5 mmol) and 2,3,4-trimethoxy-6-methylbenzaldehyde (1.04 g, 5 mmol) in ethyl alcohol (20 ml) was stirred magnetically for 2 h at reflux temperature. After cooling the precipitate was filtered and dried. The crude product of 20 mg was dissolved in a 20 ml of ethylalcohol by heating on a magnetic stirrer. The solution was filtered to remove impurities, and then left to crystallize at room temperature. After a week single crystals suitable for the X-ray crystal structure determination were obtained.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids.
	Fig. 2. Part of the crystal structure of (I).

(E)-4-Methyl-N-(2,3,4-trimethoxy-6-methylbenzylidene)aniline top

Crystal data top

C₁₈H₂₁NO₃	F(000) = 640
M_r = 299.36	D_x = 1.206 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1422 reflections
a = 7.7239 (9) Å	θ = 2.7–20.0°
b = 27.287 (2) Å	µ = 0.08 mm⁻¹
c = 8.4128 (11) Å	T = 298 K
β = 111.529 (2)°	Block, brown
V = 1649.4 (3) Å³	0.45 × 0.43 × 0.40 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2899 independent reflections
Radiation source: fine-focus sealed tube	1475 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.964, T_max = 0.968	k = −30→32
8258 measured reflections	l = −9→5

Refinement top

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0477P)² + 0.6503P] where P = (F_o² + 2F_c²)/3
2899 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₈H₂₁NO₃	V = 1649.4 (3) Å³
M_r = 299.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.7239 (9) Å	µ = 0.08 mm⁻¹
b = 27.287 (2) Å	T = 298 K
c = 8.4128 (11) Å	0.45 × 0.43 × 0.40 mm
β = 111.529 (2)°

Data collection top

Bruker SMART CCD diffractometer	2899 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1475 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.968	R_int = 0.055
8258 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.02	Δρ_max = 0.19 e Å⁻³
2899 reflections	Δρ_min = −0.18 e Å⁻³
199 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.9325 (3)	0.15463 (10)	0.3804 (4)	0.0607 (7)
O1	0.9997 (3)	0.09590 (7)	−0.0287 (2)	0.0536 (6)
O2	0.7379 (3)	0.04533 (8)	−0.2839 (3)	0.0628 (6)
O3	0.3972 (3)	0.02973 (8)	−0.2724 (3)	0.0640 (6)
C1	0.9412 (4)	0.13395 (11)	0.2492 (4)	0.0520 (8)
H1	1.0549	0.1351	0.2348	0.062*
C2	0.7898 (4)	0.10855 (10)	0.1187 (4)	0.0448 (7)
C3	0.8252 (4)	0.08912 (10)	−0.0207 (4)	0.0451 (7)
C4	0.6955 (4)	0.06230 (10)	−0.1484 (4)	0.0466 (7)
C5	0.5201 (4)	0.05545 (10)	−0.1404 (4)	0.0481 (8)
C6	0.4808 (4)	0.07464 (11)	−0.0057 (4)	0.0506 (8)
H6	0.3632	0.0698	−0.0019	0.061*
C7	0.6114 (4)	0.10096 (10)	0.1238 (4)	0.0512 (8)
C8	1.0063 (5)	0.13609 (12)	−0.1356 (5)	0.0742 (11)
H8A	0.9214	0.1302	−0.2502	0.111*
H8B	1.1303	0.1393	−0.1350	0.111*
H8C	0.9717	0.1657	−0.0933	0.111*
C9	0.7579 (5)	−0.00633 (14)	−0.2860 (5)	0.0790 (11)
H9A	0.8493	−0.0169	−0.1793	0.119*
H9B	0.7973	−0.0154	−0.3777	0.119*
H9C	0.6408	−0.0217	−0.3023	0.119*
C10	0.2178 (4)	0.01986 (14)	−0.2686 (4)	0.0737 (11)
H10A	0.2309	0.0048	−0.1617	0.111*
H10B	0.1515	−0.0018	−0.3607	0.111*
H10C	0.1499	0.0500	−0.2808	0.111*
C11	0.5545 (5)	0.11989 (13)	0.2664 (5)	0.0774 (11)
H11A	0.4251	0.1131	0.2402	0.116*
H11B	0.5749	0.1546	0.2779	0.116*
H11C	0.6275	0.1040	0.3715	0.116*
C12	1.0977 (4)	0.17428 (11)	0.5029 (4)	0.0501 (8)
C13	1.2692 (4)	0.15170 (11)	0.5499 (4)	0.0566 (9)
H13	1.2816	0.1228	0.4965	0.068*
C14	1.4218 (4)	0.17184 (12)	0.6755 (4)	0.0623 (9)
H14	1.5363	0.1562	0.7045	0.075*
C15	1.4108 (4)	0.21420 (12)	0.7595 (4)	0.0596 (9)
C16	1.2394 (5)	0.23596 (12)	0.7127 (4)	0.0678 (10)
H16	1.2272	0.2647	0.7668	0.081*
C17	1.0854 (5)	0.21645 (12)	0.5881 (4)	0.0653 (10)
H17	0.9708	0.2319	0.5607	0.078*
C18	1.5798 (5)	0.23466 (14)	0.8988 (5)	0.0950 (13)
H18A	1.6665	0.2465	0.8501	0.143*
H18B	1.6375	0.2094	0.9806	0.143*
H18C	1.5431	0.2612	0.9546	0.143*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0504 (16)	0.0693 (19)	0.0638 (19)	−0.0076 (14)	0.0229 (15)	−0.0111 (15)
O1	0.0471 (12)	0.0616 (14)	0.0591 (14)	−0.0011 (10)	0.0279 (10)	0.0078 (11)
O2	0.0767 (15)	0.0720 (16)	0.0501 (14)	−0.0086 (12)	0.0355 (12)	−0.0009 (11)
O3	0.0516 (13)	0.0881 (17)	0.0500 (14)	−0.0170 (12)	0.0159 (11)	−0.0071 (12)
C1	0.0486 (19)	0.0546 (19)	0.061 (2)	−0.0062 (15)	0.0293 (17)	0.0001 (17)
C2	0.0424 (17)	0.0433 (17)	0.0525 (19)	−0.0031 (14)	0.0220 (15)	−0.0009 (14)
C3	0.0414 (17)	0.0468 (18)	0.0517 (19)	−0.0009 (14)	0.0225 (15)	0.0067 (15)
C4	0.0497 (19)	0.0529 (19)	0.0403 (18)	−0.0016 (15)	0.0200 (15)	0.0060 (15)
C5	0.0437 (18)	0.0512 (19)	0.0470 (19)	−0.0039 (15)	0.0140 (15)	0.0036 (15)
C6	0.0449 (18)	0.0546 (19)	0.056 (2)	−0.0047 (15)	0.0224 (16)	0.0009 (16)
C7	0.0529 (19)	0.0495 (19)	0.059 (2)	−0.0036 (15)	0.0292 (17)	−0.0030 (16)
C8	0.068 (2)	0.075 (2)	0.095 (3)	−0.0027 (19)	0.048 (2)	0.023 (2)
C9	0.090 (3)	0.081 (3)	0.082 (3)	−0.008 (2)	0.051 (2)	−0.016 (2)
C10	0.053 (2)	0.099 (3)	0.063 (2)	−0.0190 (19)	0.0128 (18)	−0.003 (2)
C11	0.067 (2)	0.088 (3)	0.095 (3)	−0.021 (2)	0.052 (2)	−0.033 (2)
C12	0.0501 (19)	0.0525 (19)	0.0501 (19)	−0.0024 (16)	0.0212 (16)	0.0005 (16)
C13	0.062 (2)	0.0442 (19)	0.067 (2)	0.0038 (17)	0.0269 (19)	−0.0008 (16)
C14	0.049 (2)	0.059 (2)	0.072 (2)	0.0071 (17)	0.0150 (18)	0.0057 (19)
C15	0.059 (2)	0.051 (2)	0.061 (2)	−0.0044 (17)	0.0131 (18)	−0.0014 (17)
C16	0.068 (2)	0.056 (2)	0.075 (2)	0.0058 (19)	0.021 (2)	−0.0140 (18)
C17	0.052 (2)	0.066 (2)	0.076 (3)	0.0088 (17)	0.0201 (19)	−0.0124 (19)
C18	0.077 (3)	0.087 (3)	0.091 (3)	−0.009 (2)	−0.005 (2)	−0.012 (2)

Geometric parameters (Å, º) top

N1—C1	1.263 (3)	C9—H9B	0.9600
N1—C12	1.419 (4)	C9—H9C	0.9600
O1—C3	1.386 (3)	C10—H10A	0.9600
O1—C8	1.431 (3)	C10—H10B	0.9600
O2—C4	1.377 (3)	C10—H10C	0.9600
O2—C9	1.419 (4)	C11—H11A	0.9600
O3—C5	1.361 (3)	C11—H11B	0.9600
O3—C10	1.423 (3)	C11—H11C	0.9600
C1—C2	1.453 (4)	C12—C17	1.377 (4)
C1—H1	0.9300	C12—C13	1.380 (4)
C2—C3	1.402 (4)	C13—C14	1.376 (4)
C2—C7	1.409 (4)	C13—H13	0.9300
C3—C4	1.380 (4)	C14—C15	1.373 (4)
C4—C5	1.393 (4)	C14—H14	0.9300
C5—C6	1.380 (4)	C15—C16	1.370 (4)
C6—C7	1.384 (4)	C15—C18	1.505 (4)
C6—H6	0.9300	C16—C17	1.372 (4)
C7—C11	1.512 (4)	C16—H16	0.9300
C8—H8A	0.9600	C17—H17	0.9300
C8—H8B	0.9600	C18—H18A	0.9600
C8—H8C	0.9600	C18—H18B	0.9600
C9—H9A	0.9600	C18—H18C	0.9600

C1—N1—C12	118.8 (3)	O3—C10—H10A	109.5
C3—O1—C8	113.1 (2)	O3—C10—H10B	109.5
C4—O2—C9	113.8 (2)	H10A—C10—H10B	109.5
C5—O3—C10	118.2 (2)	O3—C10—H10C	109.5
N1—C1—C2	125.9 (3)	H10A—C10—H10C	109.5
N1—C1—H1	117.0	H10B—C10—H10C	109.5
C2—C1—H1	117.0	C7—C11—H11A	109.5
C3—C2—C7	117.6 (3)	C7—C11—H11B	109.5
C3—C2—C1	117.5 (3)	H11A—C11—H11B	109.5
C7—C2—C1	124.9 (3)	C7—C11—H11C	109.5
C4—C3—O1	118.3 (3)	H11A—C11—H11C	109.5
C4—C3—C2	122.9 (3)	H11B—C11—H11C	109.5
O1—C3—C2	118.8 (3)	C17—C12—C13	117.8 (3)
O2—C4—C3	119.9 (3)	C17—C12—N1	118.6 (3)
O2—C4—C5	121.7 (3)	C13—C12—N1	123.5 (3)
C3—C4—C5	118.3 (3)	C14—C13—C12	120.2 (3)
O3—C5—C6	124.6 (3)	C14—C13—H13	119.9
O3—C5—C4	115.4 (3)	C12—C13—H13	119.9
C6—C5—C4	120.0 (3)	C15—C14—C13	122.3 (3)
C5—C6—C7	121.8 (3)	C15—C14—H14	118.9
C5—C6—H6	119.1	C13—C14—H14	118.9
C7—C6—H6	119.1	C16—C15—C14	116.9 (3)
C6—C7—C2	119.4 (3)	C16—C15—C18	122.2 (3)
C6—C7—C11	117.5 (3)	C14—C15—C18	120.9 (3)
C2—C7—C11	123.1 (3)	C15—C16—C17	121.8 (3)
O1—C8—H8A	109.5	C15—C16—H16	119.1
O1—C8—H8B	109.5	C17—C16—H16	119.1
H8A—C8—H8B	109.5	C16—C17—C12	121.0 (3)
O1—C8—H8C	109.5	C16—C17—H17	119.5
H8A—C8—H8C	109.5	C12—C17—H17	119.5
H8B—C8—H8C	109.5	C15—C18—H18A	109.5
O2—C9—H9A	109.5	C15—C18—H18B	109.5
O2—C9—H9B	109.5	H18A—C18—H18B	109.5
H9A—C9—H9B	109.5	C15—C18—H18C	109.5
O2—C9—H9C	109.5	H18A—C18—H18C	109.5
H9A—C9—H9C	109.5	H18B—C18—H18C	109.5
H9B—C9—H9C	109.5

C12—N1—C1—C2	174.7 (3)	O3—C5—C6—C7	−179.3 (3)
N1—C1—C2—C3	178.1 (3)	C4—C5—C6—C7	0.1 (4)
N1—C1—C2—C7	−3.5 (5)	C5—C6—C7—C2	0.1 (4)
C8—O1—C3—C4	83.9 (3)	C5—C6—C7—C11	−179.3 (3)
C8—O1—C3—C2	−97.8 (3)	C3—C2—C7—C6	0.7 (4)
C7—C2—C3—C4	−1.6 (4)	C1—C2—C7—C6	−177.7 (3)
C1—C2—C3—C4	176.9 (3)	C3—C2—C7—C11	−180.0 (3)
C7—C2—C3—O1	−179.8 (2)	C1—C2—C7—C11	1.6 (5)
C1—C2—C3—O1	−1.3 (4)	C1—N1—C12—C17	145.4 (3)
C9—O2—C4—C3	110.9 (3)	C1—N1—C12—C13	−39.0 (4)
C9—O2—C4—C5	−72.6 (3)	C17—C12—C13—C14	−1.3 (5)
O1—C3—C4—O2	−3.4 (4)	N1—C12—C13—C14	−177.0 (3)
C2—C3—C4—O2	178.4 (3)	C12—C13—C14—C15	0.6 (5)
O1—C3—C4—C5	180.0 (2)	C13—C14—C15—C16	0.0 (5)
C2—C3—C4—C5	1.8 (4)	C13—C14—C15—C18	178.7 (3)
C10—O3—C5—C6	−2.9 (4)	C14—C15—C16—C17	0.2 (5)
C10—O3—C5—C4	177.7 (3)	C18—C15—C16—C17	−178.5 (3)
O2—C4—C5—O3	1.9 (4)	C15—C16—C17—C12	−0.9 (5)
C3—C4—C5—O3	178.4 (2)	C13—C12—C17—C16	1.5 (5)
O2—C4—C5—C6	−177.5 (3)	N1—C12—C17—C16	177.4 (3)
C3—C4—C5—C6	−1.0 (4)

Experimental details

Crystal data
Chemical formula	C₁₈H₂₁NO₃
M_r	299.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.7239 (9), 27.287 (2), 8.4128 (11)
β (°)	111.529 (2)
V (Å³)	1649.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.45 × 0.43 × 0.40

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.964, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	8258, 2899, 1475
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.150, 1.02
No. of reflections	2899
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.18

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, C.-Y. (2009). Acta Cryst. E65, o56. Web of Science CSD CrossRef IUCr Journals Google Scholar