4-[(E)-(2-Methoxy­phen­yl)imino­meth­yl]-N,N-dimethyl­aniline

Liu, S.-B.; Bi, C.-F.; Wang, Q.; Zuo, J.; Fan, Y.-H.

doi:10.1107/S1600536810017228

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1361

https://doi.org/10.1107/S1600536810017228

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4-[(E)-(2-Methoxyphenyl)iminomethyl]-N,N-dimethylaniline

Shan-Bin Liu,^a ^* Cai-Feng Bi,^a Qiang Wang,^a Jian Zuo ^a and Yu-Hua Fan ^a

^aKey Laboratory of Marine Chemistry Theory and Technology, Ministry of Education, College of Chemistry and Chemical Engineering, Ocean University of China, Qingdao, Shandong 266100, People's Republic of China
^*Correspondence e-mail: bamboo19830406@163.com

(Received 26 April 2010; accepted 11 May 2010; online 15 May 2010)

In the title compound, C₁₆H₁₈N₂O, the dihedral angle between the benzene rings is 38.5 (2)°. The crystal packing is stabilized by weak C—H⋯N and C—H⋯O interactions and aromatic π–π stacking [centroid–centroid separations = 3.620 (5) and 3.546 (4) Å].

Related literature

For general background to Schiff bases, see: Atwood & Harvey (2001 ). For a related structure, see: Liu et al. (2009 ).

Experimental

Crystal data

C₁₆H₁₈N₂O
M_r = 254.32
Orthorhombic, P n a 2₁
a = 15.182 (8) Å
b = 11.756 (6) Å
c = 7.809 (4) Å
V = 1393.8 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.60 × 0.58 × 0.49 mm

Data collection

Siemens SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Siemens, 1996 ) T_min = 0.956, T_max = 0.963
6900 measured reflections
2335 independent reflections
1554 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.123
S = 1.01
2335 reflections
172 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8C⋯N1ⁱ	0.96	2.67	3.620 (5)	170
C4—H4⋯O1ⁱ	0.93	2.64	3.546 (4)	166
Symmetry code: (i) $[-x, -y+2, z-{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); 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: https://doi.org/10.1107/S1600536810017228/hb5420sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810017228/hb5420Isup2.hkl

checkCIF report

Comment top

Schiff base ligands are among the most fundamental chelating systems in coordination chemistry (e.g. Atwood & Harvey, 2001). Herein, we present the synthesis and structure of a new schiff base ligand, 4-{(E)-[(2-methoxyphenyl)imino]methyl}-N,N-dimethylaniline.

The crystal structure of the title compound is given in Fig. 1. The bond lengths and angles (Table 1) in the title compound are found to have normal values (Liu et al., 2009). This compound has a non-planar molecular structure, the dihedral angle between the two benzene rings is 38.54 °. In the crystal, the adjacent molecules are stabilized by non-classical C—H···N and C—H···O hydrogen bonding, with the distance of 3.620 (5) and 3.546 (4) Å (Table 2), respectively. Molecules are linked into chain along the c axis by the above weak interactions (Fig. 2).

Related literature top

For general background to Schiff bases, see: Atwood & Harvey (2001). For a related structure, see: Liu et al. (2009).

Experimental top

4-(dimethylamino) benzaldehyde (10 mmol, 1.492 g) was added with stirring to anhydrous ethanol (30 ml) and an anhydrous ethanol solution (10 ml) of 2-methoxybenzenamine (10 mmol, 1.232 g) was slowly added. The reaction mixture was stirred at 353 K for 4 h, a yellow solid then separated out. The precipitate formed was filtered off, washed several times with anhydrous ethanol and dried under vacuum. Yellow blocks of (I) were obtained from anhydrous ethanol solution after 10 days by slow evaporation at room temperature.

Structure description top

For general background to Schiff bases, see: Atwood & Harvey (2001). For a related structure, see: Liu et al. (2009).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 structure of (I) showing 30% probability displacement ellipsoids.
	Fig. 2. A view of the crystal structure of (I) showing chain to the c linked via C—H···N and C—H···O contacts.

4-[(E)-(2-Methoxyphenyl)iminomethyl]-N,N-dimethylaniline top

Crystal data top

C₁₆H₁₈N₂O	F(000) = 544
M_r = 254.32	D_x = 1.212 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1616 reflections
a = 15.182 (8) Å	θ = 2.7–21.5°
b = 11.756 (6) Å	µ = 0.08 mm⁻¹
c = 7.809 (4) Å	T = 298 K
V = 1393.8 (13) Å³	Block, yellow
Z = 4	0.60 × 0.58 × 0.49 mm

Data collection top

Siemens SMART CCD diffractometer	2335 independent reflections
Radiation source: fine-focus sealed tube	1554 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
φ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −17→18
T_min = 0.956, T_max = 0.963	k = −13→11
6900 measured reflections	l = −9→9

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0524P)² + 0.2535P] where P = (F_o² + 2F_c²)/3
2335 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.16 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₆H₁₈N₂O	V = 1393.8 (13) Å³
M_r = 254.32	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 15.182 (8) Å	µ = 0.08 mm⁻¹
b = 11.756 (6) Å	T = 298 K
c = 7.809 (4) Å	0.60 × 0.58 × 0.49 mm

Data collection top

Siemens SMART CCD diffractometer	2335 independent reflections
Absorption correction: multi-scan (SADABS; Siemens, 1996)	1554 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.963	R_int = 0.055
6900 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	1 restraint
wR(F²) = 0.123	H-atom parameters constrained
S = 1.01	Δρ_max = 0.16 e Å⁻³
2335 reflections	Δρ_min = −0.18 e Å⁻³
172 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.08529 (16)	0.7420 (2)	1.1920 (4)	0.0457 (6)
N2	0.1439 (2)	1.0507 (2)	0.5158 (4)	0.0597 (8)
O1	−0.04554 (14)	0.71462 (18)	1.4179 (3)	0.0612 (6)
C1	0.10910 (19)	0.7230 (3)	1.0385 (5)	0.0483 (8)
H1	0.1249	0.6490	1.0095	0.058*
C2	0.11330 (18)	0.8091 (2)	0.9052 (4)	0.0441 (7)
C3	0.0861 (2)	0.9208 (2)	0.9266 (5)	0.0498 (8)
H3	0.0622	0.9424	1.0313	0.060*
C4	0.0930 (2)	1.0008 (3)	0.7990 (4)	0.0488 (8)
H4	0.0721	1.0742	0.8172	0.059*
C5	0.1316 (2)	0.9720 (3)	0.6405 (4)	0.0441 (8)
C6	0.1559 (2)	0.8582 (3)	0.6161 (4)	0.0486 (8)
H6	0.1789	0.8354	0.5112	0.058*
C7	0.1464 (2)	0.7804 (3)	0.7451 (4)	0.0490 (9)
H7	0.1628	0.7053	0.7247	0.059*
C8	0.1310 (2)	1.1711 (3)	0.5473 (6)	0.0668 (10)
H8A	0.1425	1.2130	0.4441	0.100*
H8B	0.1706	1.1959	0.6356	0.100*
H8C	0.0714	1.1843	0.5832	0.100*
C9	0.1775 (3)	1.0189 (3)	0.3522 (5)	0.0838 (13)
H9A	0.1816	1.0850	0.2805	0.126*
H9B	0.1386	0.9645	0.3003	0.126*
H9C	0.2349	0.9858	0.3656	0.126*
C10	0.09047 (19)	0.6513 (2)	1.3124 (4)	0.0419 (7)
C11	0.0228 (2)	0.6391 (2)	1.4323 (4)	0.0455 (7)
C12	0.0272 (2)	0.5535 (2)	1.5526 (5)	0.0535 (8)
H12	−0.0182	0.5450	1.6315	0.064*
C13	0.0982 (2)	0.4804 (3)	1.5570 (5)	0.0613 (9)
H13	0.1005	0.4228	1.6385	0.074*
C14	0.1645 (2)	0.4925 (3)	1.4428 (5)	0.0600 (9)
H14	0.2124	0.4433	1.4462	0.072*
C15	0.1615 (2)	0.5780 (2)	1.3207 (5)	0.0522 (8)
H15	0.2077	0.5861	1.2435	0.063*
C16	−0.1075 (3)	0.7158 (4)	1.5491 (7)	0.1119 (18)
H16A	−0.1517	0.7718	1.5246	0.168*
H16B	−0.0789	0.7341	1.6553	0.168*
H16C	−0.1345	0.6422	1.5578	0.168*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0510 (15)	0.0398 (15)	0.0465 (16)	−0.0020 (12)	0.0057 (14)	0.0021 (13)
N2	0.082 (2)	0.0495 (17)	0.0477 (19)	0.0023 (15)	0.0034 (16)	0.0051 (14)
O1	0.0611 (14)	0.0659 (14)	0.0565 (14)	0.0128 (11)	0.0183 (14)	0.0079 (13)
C1	0.0491 (18)	0.0401 (17)	0.056 (2)	−0.0014 (13)	0.0061 (17)	−0.0022 (18)
C2	0.0444 (16)	0.0412 (17)	0.047 (2)	−0.0059 (14)	0.0060 (16)	0.0013 (16)
C3	0.0525 (18)	0.0463 (17)	0.0506 (19)	0.0001 (14)	0.0084 (18)	−0.0012 (18)
C4	0.0532 (19)	0.0412 (17)	0.052 (2)	0.0033 (15)	−0.0015 (18)	−0.0010 (17)
C5	0.0472 (18)	0.0457 (18)	0.0393 (19)	−0.0050 (14)	−0.0056 (15)	0.0044 (16)
C6	0.0574 (19)	0.051 (2)	0.0379 (18)	−0.0011 (15)	0.0008 (15)	−0.0072 (16)
C7	0.057 (2)	0.0390 (18)	0.051 (2)	−0.0002 (15)	−0.0008 (16)	−0.0017 (16)
C8	0.072 (2)	0.051 (2)	0.077 (2)	0.0034 (17)	−0.005 (2)	0.0163 (19)
C9	0.123 (4)	0.070 (3)	0.058 (3)	−0.007 (2)	0.006 (3)	0.011 (2)
C10	0.0513 (18)	0.0315 (15)	0.0430 (18)	−0.0035 (14)	0.0018 (16)	−0.0028 (15)
C11	0.0547 (18)	0.0434 (17)	0.0383 (17)	−0.0013 (14)	0.0023 (17)	−0.0032 (16)
C12	0.061 (2)	0.0488 (19)	0.050 (2)	−0.0071 (16)	0.0132 (18)	0.0029 (17)
C13	0.076 (2)	0.0470 (19)	0.061 (2)	0.0001 (18)	−0.004 (2)	0.0091 (19)
C14	0.057 (2)	0.0491 (19)	0.074 (3)	0.0080 (15)	0.004 (2)	0.011 (2)
C15	0.0488 (18)	0.0497 (19)	0.058 (2)	−0.0004 (15)	0.0052 (17)	0.0025 (18)
C16	0.108 (3)	0.122 (4)	0.106 (4)	0.047 (3)	0.061 (3)	0.035 (3)

Geometric parameters (Å, º) top

N1—C1	1.272 (4)	C8—H8A	0.9600
N1—C10	1.423 (4)	C8—H8B	0.9600
N2—C5	1.356 (4)	C8—H8C	0.9600
N2—C9	1.425 (5)	C9—H9A	0.9600
N2—C8	1.450 (4)	C9—H9B	0.9600
O1—C11	1.370 (3)	C9—H9C	0.9600
O1—C16	1.390 (5)	C10—C15	1.382 (4)
C1—C2	1.453 (5)	C10—C11	1.398 (4)
C1—H1	0.9300	C11—C12	1.378 (4)
C2—C3	1.387 (4)	C12—C13	1.379 (4)
C2—C7	1.390 (4)	C12—H12	0.9300
C3—C4	1.374 (4)	C13—C14	1.353 (5)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.410 (4)	C14—C15	1.386 (4)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.401 (4)	C15—H15	0.9300
C6—C7	1.368 (4)	C16—H16A	0.9600
C6—H6	0.9300	C16—H16B	0.9600
C7—H7	0.9300	C16—H16C	0.9600

C1—N1—C10	118.4 (3)	H8B—C8—H8C	109.5
C5—N2—C9	120.9 (3)	N2—C9—H9A	109.5
C5—N2—C8	121.7 (3)	N2—C9—H9B	109.5
C9—N2—C8	117.2 (3)	H9A—C9—H9B	109.5
C11—O1—C16	117.3 (3)	N2—C9—H9C	109.5
N1—C1—C2	124.4 (3)	H9A—C9—H9C	109.5
N1—C1—H1	117.8	H9B—C9—H9C	109.5
C2—C1—H1	117.8	C15—C10—C11	118.6 (3)
C3—C2—C7	116.5 (3)	C15—C10—N1	122.8 (3)
C3—C2—C1	124.1 (3)	C11—C10—N1	118.6 (3)
C7—C2—C1	119.4 (3)	O1—C11—C12	124.4 (3)
C4—C3—C2	122.5 (3)	O1—C11—C10	115.8 (3)
C4—C3—H3	118.7	C12—C11—C10	119.7 (3)
C2—C3—H3	118.7	C11—C12—C13	120.7 (3)
C3—C4—C5	120.3 (3)	C11—C12—H12	119.7
C3—C4—H4	119.9	C13—C12—H12	119.7
C5—C4—H4	119.9	C14—C13—C12	120.0 (3)
N2—C5—C6	121.2 (3)	C14—C13—H13	120.0
N2—C5—C4	121.6 (3)	C12—C13—H13	120.0
C6—C5—C4	117.3 (3)	C13—C14—C15	120.3 (3)
C7—C6—C5	120.7 (3)	C13—C14—H14	119.8
C7—C6—H6	119.6	C15—C14—H14	119.8
C5—C6—H6	119.6	C10—C15—C14	120.7 (3)
C6—C7—C2	122.6 (3)	C10—C15—H15	119.6
C6—C7—H7	118.7	C14—C15—H15	119.6
C2—C7—H7	118.7	O1—C16—H16A	109.5
N2—C8—H8A	109.5	O1—C16—H16B	109.5
N2—C8—H8B	109.5	H16A—C16—H16B	109.5
H8A—C8—H8B	109.5	O1—C16—H16C	109.5
N2—C8—H8C	109.5	H16A—C16—H16C	109.5
H8A—C8—H8C	109.5	H16B—C16—H16C	109.5

C10—N1—C1—C2	−175.4 (3)	C1—C2—C7—C6	−177.0 (3)
N1—C1—C2—C3	−4.6 (5)	C1—N1—C10—C15	42.7 (4)
N1—C1—C2—C7	175.3 (3)	C1—N1—C10—C11	−140.4 (3)
C7—C2—C3—C4	−1.6 (5)	C16—O1—C11—C12	10.2 (5)
C1—C2—C3—C4	178.4 (3)	C16—O1—C11—C10	−170.9 (4)
C2—C3—C4—C5	−2.1 (5)	C15—C10—C11—O1	179.7 (3)
C9—N2—C5—C6	3.6 (5)	N1—C10—C11—O1	2.5 (4)
C8—N2—C5—C6	−170.9 (3)	C15—C10—C11—C12	−1.5 (4)
C9—N2—C5—C4	−175.8 (3)	N1—C10—C11—C12	−178.6 (3)
C8—N2—C5—C4	9.8 (5)	O1—C11—C12—C13	179.4 (3)
C3—C4—C5—N2	−176.2 (3)	C10—C11—C12—C13	0.7 (5)
C3—C4—C5—C6	4.5 (4)	C11—C12—C13—C14	0.2 (5)
N2—C5—C6—C7	177.4 (3)	C12—C13—C14—C15	−0.1 (5)
C4—C5—C6—C7	−3.2 (4)	C11—C10—C15—C14	1.5 (4)
C5—C6—C7—C2	−0.5 (5)	N1—C10—C15—C14	178.5 (3)
C3—C2—C7—C6	2.9 (5)	C13—C14—C15—C10	−0.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8C···N1ⁱ	0.96	2.67	3.620 (5)	170
C4—H4···O1ⁱ	0.93	2.64	3.546 (4)	166

Symmetry code: (i) −x, −y+2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₈N₂O
M_r	254.32
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	298
a, b, c (Å)	15.182 (8), 11.756 (6), 7.809 (4)
V (Å³)	1393.8 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.60 × 0.58 × 0.49

Data collection
Diffractometer	Siemens SMART CCD
Absorption correction	Multi-scan (SADABS; Siemens, 1996)
T_min, T_max	0.956, 0.963
No. of measured, independent and observed [I > 2σ(I)] reflections	6900, 2335, 1554
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.123, 1.01
No. of reflections	2335
No. of parameters	172
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.18

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

N1—C1	1.272 (4)	C1—C2	1.453 (5)
N1—C10	1.423 (4)

C1—N1—C10	118.4 (3)	C11—C10—N1	118.6 (3)
N1—C1—C2	124.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8C···N1ⁱ	0.96	2.67	3.620 (5)	170
C4—H4···O1ⁱ	0.93	2.64	3.546 (4)	166

Symmetry code: (i) −x, −y+2, z−1/2.

Acknowledgements

The authors acknowledge the National Science Foundation of China for its financial support of this project (grant No. 20971115).

References

Atwood, D. A. & Harvey, M. J. (2001). Chem. Rev. 101, 37–52. Web of Science CrossRef PubMed CAS Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar