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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): o1361.
Published online 2010 May 15. doi:  10.1107/S1600536810017228
PMCID: PMC2979452

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

Abstract

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 [triangle]). For a related structure, see: Liu et al. (2009 [triangle]).

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Object name is e-66-o1361-scheme1.jpg

Experimental

Crystal data

  • C16H18N2O
  • M r = 254.32
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1361-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.123
  • S = 1.01
  • 2335 reflections
  • 172 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810017228/hb5420sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017228/hb5420Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

The absolute structure of (I) is indeterminate based on the present refinement. All H-atoms were positioned geometrically and refined using a riding model, with C—H = 0.96 Å (methyl), 0.93 Å (methenyl), 0.93 Å (aromatic), and Uiso(H) =1.2Ueq(C).

Figures

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.

Crystal data

C16H18N2OF(000) = 544
Mr = 254.32Dx = 1.212 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 1616 reflections
a = 15.182 (8) Åθ = 2.7–21.5°
b = 11.756 (6) ŵ = 0.08 mm1
c = 7.809 (4) ÅT = 298 K
V = 1393.8 (13) Å3Block, yellow
Z = 40.60 × 0.58 × 0.49 mm

Data collection

Siemens SMART CCD diffractometer2335 independent reflections
Radiation source: fine-focus sealed tube1554 reflections with I > 2σ(I)
graphiteRint = 0.055
[var phi] and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Siemens, 1996)h = −17→18
Tmin = 0.956, Tmax = 0.963k = −13→11
6900 measured reflectionsl = −9→9

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0524P)2 + 0.2535P] where P = (Fo2 + 2Fc2)/3
2335 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.16 e Å3
1 restraintΔρmin = −0.17 e Å3

Special details

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)

xyzUiso*/Ueq
N10.08529 (16)0.7420 (2)1.1920 (4)0.0457 (6)
N20.1439 (2)1.0507 (2)0.5158 (4)0.0597 (8)
O1−0.04554 (14)0.71462 (18)1.4179 (3)0.0612 (6)
C10.10910 (19)0.7230 (3)1.0385 (5)0.0483 (8)
H10.12490.64901.00950.058*
C20.11330 (18)0.8091 (2)0.9052 (4)0.0441 (7)
C30.0861 (2)0.9208 (2)0.9266 (5)0.0498 (8)
H30.06220.94241.03130.060*
C40.0930 (2)1.0008 (3)0.7990 (4)0.0488 (8)
H40.07211.07420.81720.059*
C50.1316 (2)0.9720 (3)0.6405 (4)0.0441 (8)
C60.1559 (2)0.8582 (3)0.6161 (4)0.0486 (8)
H60.17890.83540.51120.058*
C70.1464 (2)0.7804 (3)0.7451 (4)0.0490 (9)
H70.16280.70530.72470.059*
C80.1310 (2)1.1711 (3)0.5473 (6)0.0668 (10)
H8A0.14251.21300.44410.100*
H8B0.17061.19590.63560.100*
H8C0.07141.18430.58320.100*
C90.1775 (3)1.0189 (3)0.3522 (5)0.0838 (13)
H9A0.18161.08500.28050.126*
H9B0.13860.96450.30030.126*
H9C0.23490.98580.36560.126*
C100.09047 (19)0.6513 (2)1.3124 (4)0.0419 (7)
C110.0228 (2)0.6391 (2)1.4323 (4)0.0455 (7)
C120.0272 (2)0.5535 (2)1.5526 (5)0.0535 (8)
H12−0.01820.54501.63150.064*
C130.0982 (2)0.4804 (3)1.5570 (5)0.0613 (9)
H130.10050.42281.63850.074*
C140.1645 (2)0.4925 (3)1.4428 (5)0.0600 (9)
H140.21240.44331.44620.072*
C150.1615 (2)0.5780 (2)1.3207 (5)0.0522 (8)
H150.20770.58611.24350.063*
C16−0.1075 (3)0.7158 (4)1.5491 (7)0.1119 (18)
H16A−0.15170.77181.52460.168*
H16B−0.07890.73411.65530.168*
H16C−0.13450.64221.55780.168*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0510 (15)0.0398 (15)0.0465 (16)−0.0020 (12)0.0057 (14)0.0021 (13)
N20.082 (2)0.0495 (17)0.0477 (19)0.0023 (15)0.0034 (16)0.0051 (14)
O10.0611 (14)0.0659 (14)0.0565 (14)0.0128 (11)0.0183 (14)0.0079 (13)
C10.0491 (18)0.0401 (17)0.056 (2)−0.0014 (13)0.0061 (17)−0.0022 (18)
C20.0444 (16)0.0412 (17)0.047 (2)−0.0059 (14)0.0060 (16)0.0013 (16)
C30.0525 (18)0.0463 (17)0.0506 (19)0.0001 (14)0.0084 (18)−0.0012 (18)
C40.0532 (19)0.0412 (17)0.052 (2)0.0033 (15)−0.0015 (18)−0.0010 (17)
C50.0472 (18)0.0457 (18)0.0393 (19)−0.0050 (14)−0.0056 (15)0.0044 (16)
C60.0574 (19)0.051 (2)0.0379 (18)−0.0011 (15)0.0008 (15)−0.0072 (16)
C70.057 (2)0.0390 (18)0.051 (2)−0.0002 (15)−0.0008 (16)−0.0017 (16)
C80.072 (2)0.051 (2)0.077 (2)0.0034 (17)−0.005 (2)0.0163 (19)
C90.123 (4)0.070 (3)0.058 (3)−0.007 (2)0.006 (3)0.011 (2)
C100.0513 (18)0.0315 (15)0.0430 (18)−0.0035 (14)0.0018 (16)−0.0028 (15)
C110.0547 (18)0.0434 (17)0.0383 (17)−0.0013 (14)0.0023 (17)−0.0032 (16)
C120.061 (2)0.0488 (19)0.050 (2)−0.0071 (16)0.0132 (18)0.0029 (17)
C130.076 (2)0.0470 (19)0.061 (2)0.0001 (18)−0.004 (2)0.0091 (19)
C140.057 (2)0.0491 (19)0.074 (3)0.0080 (15)0.004 (2)0.011 (2)
C150.0488 (18)0.0497 (19)0.058 (2)−0.0004 (15)0.0052 (17)0.0025 (18)
C160.108 (3)0.122 (4)0.106 (4)0.047 (3)0.061 (3)0.035 (3)

Geometric parameters (Å, °)

N1—C11.272 (4)C8—H8A0.9600
N1—C101.423 (4)C8—H8B0.9600
N2—C51.356 (4)C8—H8C0.9600
N2—C91.425 (5)C9—H9A0.9600
N2—C81.450 (4)C9—H9B0.9600
O1—C111.370 (3)C9—H9C0.9600
O1—C161.390 (5)C10—C151.382 (4)
C1—C21.453 (5)C10—C111.398 (4)
C1—H10.9300C11—C121.378 (4)
C2—C31.387 (4)C12—C131.379 (4)
C2—C71.390 (4)C12—H120.9300
C3—C41.374 (4)C13—C141.353 (5)
C3—H30.9300C13—H130.9300
C4—C51.410 (4)C14—C151.386 (4)
C4—H40.9300C14—H140.9300
C5—C61.401 (4)C15—H150.9300
C6—C71.368 (4)C16—H16A0.9600
C6—H60.9300C16—H16B0.9600
C7—H70.9300C16—H16C0.9600
C1—N1—C10118.4 (3)H8B—C8—H8C109.5
C5—N2—C9120.9 (3)N2—C9—H9A109.5
C5—N2—C8121.7 (3)N2—C9—H9B109.5
C9—N2—C8117.2 (3)H9A—C9—H9B109.5
C11—O1—C16117.3 (3)N2—C9—H9C109.5
N1—C1—C2124.4 (3)H9A—C9—H9C109.5
N1—C1—H1117.8H9B—C9—H9C109.5
C2—C1—H1117.8C15—C10—C11118.6 (3)
C3—C2—C7116.5 (3)C15—C10—N1122.8 (3)
C3—C2—C1124.1 (3)C11—C10—N1118.6 (3)
C7—C2—C1119.4 (3)O1—C11—C12124.4 (3)
C4—C3—C2122.5 (3)O1—C11—C10115.8 (3)
C4—C3—H3118.7C12—C11—C10119.7 (3)
C2—C3—H3118.7C11—C12—C13120.7 (3)
C3—C4—C5120.3 (3)C11—C12—H12119.7
C3—C4—H4119.9C13—C12—H12119.7
C5—C4—H4119.9C14—C13—C12120.0 (3)
N2—C5—C6121.2 (3)C14—C13—H13120.0
N2—C5—C4121.6 (3)C12—C13—H13120.0
C6—C5—C4117.3 (3)C13—C14—C15120.3 (3)
C7—C6—C5120.7 (3)C13—C14—H14119.8
C7—C6—H6119.6C15—C14—H14119.8
C5—C6—H6119.6C10—C15—C14120.7 (3)
C6—C7—C2122.6 (3)C10—C15—H15119.6
C6—C7—H7118.7C14—C15—H15119.6
C2—C7—H7118.7O1—C16—H16A109.5
N2—C8—H8A109.5O1—C16—H16B109.5
N2—C8—H8B109.5H16A—C16—H16B109.5
H8A—C8—H8B109.5O1—C16—H16C109.5
N2—C8—H8C109.5H16A—C16—H16C109.5
H8A—C8—H8C109.5H16B—C16—H16C109.5
C10—N1—C1—C2−175.4 (3)C1—C2—C7—C6−177.0 (3)
N1—C1—C2—C3−4.6 (5)C1—N1—C10—C1542.7 (4)
N1—C1—C2—C7175.3 (3)C1—N1—C10—C11−140.4 (3)
C7—C2—C3—C4−1.6 (5)C16—O1—C11—C1210.2 (5)
C1—C2—C3—C4178.4 (3)C16—O1—C11—C10−170.9 (4)
C2—C3—C4—C5−2.1 (5)C15—C10—C11—O1179.7 (3)
C9—N2—C5—C63.6 (5)N1—C10—C11—O12.5 (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—C49.8 (5)O1—C11—C12—C13179.4 (3)
C3—C4—C5—N2−176.2 (3)C10—C11—C12—C130.7 (5)
C3—C4—C5—C64.5 (4)C11—C12—C13—C140.2 (5)
N2—C5—C6—C7177.4 (3)C12—C13—C14—C15−0.1 (5)
C4—C5—C6—C7−3.2 (4)C11—C10—C15—C141.5 (4)
C5—C6—C7—C2−0.5 (5)N1—C10—C15—C14178.5 (3)
C3—C2—C7—C62.9 (5)C13—C14—C15—C10−0.7 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C8—H8C···N1i0.962.673.620 (5)170
C4—H4···O1i0.932.643.546 (4)166

Symmetry codes: (i) −x, −y+2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5420).

References

  • Atwood, D. A. & Harvey, M. J. (2001). Chem. Rev.101, 37–52. [PubMed]
  • Liu, X.-Y., Fan, Y.-H., Bi, C.-F., Wang, Q. & Gao, Y. (2009). Acta Cryst. E65, o2170. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART, SAINT and SADABS Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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