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Acta Cryst. (2009). E65, o506    [ doi:10.1107/S1600536809003791 ]

N,N-Dimethyl-4-[(E)-phenyliminomethyl]aniline

L. Zheng, X. Yin, C. Yang, Y. Li and S. Yin

Abstract top

The title compound, C15H16N2, contains two aromatic rings linked through an imino group. The molecule exhibits an E configuration with respect to the C=N bond. The dihedral angle between the aromatic rings is 61.96 (1)°.

Comment top

Schiff base, because of its unique light, electric, magnetic and other physical material properties (Tang & Vanslyke, 1987; Yu et al., 2001), good coordination chemistry performance, unique anti-bacterial, anti-cancer and other physiological activities (Nyarku & Mavuso, 1998; Hodnett & Dunn, 1970), has aroused broad, systematic and in-depth theoretical and applied research. Several crystal sturctures of schiff bases, which are closely related to the title compound, have been reported (eg., Ahmet et al., 1994; Nakai et al., 1976; Wang & Wang, 2008; Wang & Wang, 2007). We report herein the crystal sturcture of the title schiff base, N,N-dimethyl-4-[(E)-(phenylimino)methyl]benzenamine, (I).

The molecule of the title compound (Fig. 1) adopts an E configuration probably owing to the steric effect. The C(10)–N(2)–C(9)–C(6) and C(7)–C(6)–C(9)–N(2) torsion angles are -176.70 (15) and 9.2 (3)°, respectively. There are no intermolecular hydrogen-bonding interactions in the crystal structure. The packing is essentially stabilized via van der Waals forces.

Related literature top

For background literature, see: Hodnett & Dunn (1970); Nyarku & Mavuso (1998); Tang & Vanslyke (1987); Yu et al. (2001). For related structures, see: Ahmet et al. (1994); Nakai et al. (1976); Wang & Wang (2007, 2008).

Experimental top

To a solution of N,N-dimethyl-4-aminobenzaldehyde (0.75 g, 5 mmol) in ethanol (10 ml) and aniline (0.91 ml, 10 mmol) were added three drops of acetic acid as a catalyst. The mixture was heated to reflux and the reaction monitored by TLC. After completion of the reaction, on cooling to room temperature, crystals were obtained. Colourless crystals suitable for X-ray analysis were obtained by slow evaporation of an ethyl acetate solution at room temperature.

Refinement top

H atoms were positioned geometrically (C—H = 0.93–0.96 Å) and included in the refinement using a riding model, with Uiso(H) = 1.2Ueq (methylene C, aromatic C), Uiso(H) = 1.5Ueq (methyl C).

Computing details top

Data collection: DIFRAC (Gabe et al., 1993); cell refinement: NRCVAX (Gabe et al., 1989); data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia,1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level.
N,N-Dimethyl-4-[(E)-phenyliminomethyl]aniline top
Crystal data top
C15H16N2F(000) = 480
Mr = 224.30Dx = 1.173 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 20 reflections
a = 9.441 (4) Åθ = 4.4–7.1°
b = 8.356 (3) ŵ = 0.07 mm−1
c = 17.245 (5) ÅT = 292 K
β = 110.97 (2)°Block, colourless
V = 1270.4 (8) Å30.52 × 0.48 × 0.46 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.012
Radiation source: fine-focus sealed tubeθmax = 25.5°, θmin = 2.3°
graphiteh = −11→11
ω/2θ scansk = −10→0
3023 measured reflectionsl = −20→10
2328 independent reflections3 standard reflections every 200 reflections
1336 reflections with I > 2σ(I) intensity decay: 1.8%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.150 w = 1/[σ2(Fo2) + (0.0913P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2328 reflectionsΔρmax = 0.13 e Å−3
157 parametersΔρmin = −0.13 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.032 (10)
Crystal data top
C15H16N2V = 1270.4 (8) Å3
Mr = 224.30Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.441 (4) ŵ = 0.07 mm−1
b = 8.356 (3) ÅT = 292 K
c = 17.245 (5) Å0.52 × 0.48 × 0.46 mm
β = 110.97 (2)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.012
3023 measured reflectionsθmax = 25.5°
2328 independent reflections3 standard reflections every 200 reflections
1336 reflections with I > 2σ(I) intensity decay: 1.8%
Refinement top
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.150Δρmax = 0.13 e Å−3
S = 1.02Δρmin = −0.13 e Å−3
2328 reflectionsAbsolute structure: ?
157 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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 > 2σ(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
xyzUiso*/Ueq
N10.30901 (17)1.50607 (18)−0.07311 (10)0.0722 (5)
N20.28787 (18)0.86291 (19)0.13032 (9)0.0668 (5)
C10.3837 (2)1.4806 (2)−0.13194 (12)0.0815 (6)
H1A0.48311.4372−0.10370.122*
H1B0.39241.5807−0.15720.122*
H1C0.32541.4071−0.17400.122*
C20.2456 (3)1.6630 (2)−0.07117 (15)0.0907 (7)
H2A0.13691.6571−0.09440.136*
H2B0.28101.7363−0.10310.136*
H2C0.27681.6997−0.01480.136*
C30.28724 (19)1.3833 (2)−0.02654 (11)0.0587 (5)
C40.2055 (2)1.4036 (2)0.02656 (12)0.0687 (5)
H40.16361.50290.03000.082*
C50.1867 (2)1.2792 (2)0.07319 (12)0.0686 (5)
H50.13291.29650.10820.082*
C60.2449 (2)1.1275 (2)0.07036 (11)0.0616 (5)
C70.3258 (2)1.1071 (2)0.01746 (10)0.0636 (5)
H70.36691.00730.01420.076*
C80.3462 (2)1.2297 (2)−0.02946 (11)0.0625 (5)
H80.40041.2115−0.06430.075*
C90.2222 (2)0.9985 (2)0.12090 (11)0.0681 (5)
H90.15501.01600.14840.082*
C100.2496 (2)0.7447 (2)0.17785 (11)0.0619 (5)
C110.1006 (2)0.7114 (2)0.16925 (12)0.0715 (6)
H110.02170.77020.13210.086*
C120.0694 (2)0.5918 (3)0.21553 (13)0.0795 (6)
H12−0.03070.57000.20930.095*
C130.1848 (3)0.5041 (2)0.27093 (13)0.0796 (6)
H130.16290.42430.30250.096*
C140.3326 (2)0.5352 (2)0.27936 (12)0.0744 (6)
H140.41100.47570.31650.089*
C150.3645 (2)0.6536 (2)0.23315 (11)0.0682 (5)
H150.46480.67330.23890.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0775 (11)0.0677 (10)0.0723 (11)0.0087 (8)0.0278 (9)0.0044 (8)
N20.0681 (10)0.0769 (11)0.0590 (9)0.0019 (8)0.0270 (8)−0.0015 (8)
C10.0882 (14)0.0911 (14)0.0695 (12)−0.0005 (11)0.0338 (11)0.0092 (11)
C20.0945 (16)0.0719 (13)0.1018 (16)0.0086 (11)0.0305 (14)0.0059 (12)
C30.0538 (10)0.0656 (11)0.0530 (10)−0.0001 (8)0.0146 (8)−0.0077 (9)
C40.0696 (12)0.0667 (11)0.0716 (12)0.0094 (9)0.0276 (10)−0.0083 (10)
C50.0684 (12)0.0816 (14)0.0637 (11)0.0060 (10)0.0333 (10)−0.0109 (10)
C60.0620 (11)0.0713 (12)0.0535 (10)0.0026 (9)0.0231 (9)−0.0057 (9)
C70.0682 (12)0.0637 (11)0.0630 (11)0.0070 (9)0.0285 (10)−0.0066 (9)
C80.0669 (12)0.0682 (12)0.0580 (11)0.0063 (9)0.0290 (9)−0.0048 (9)
C90.0657 (12)0.0836 (14)0.0594 (11)0.0019 (10)0.0278 (9)−0.0064 (10)
C100.0642 (12)0.0724 (11)0.0528 (10)−0.0030 (10)0.0255 (9)−0.0095 (9)
C110.0607 (12)0.0852 (14)0.0656 (12)−0.0022 (10)0.0191 (10)−0.0030 (11)
C120.0657 (12)0.0961 (15)0.0779 (13)−0.0151 (11)0.0271 (11)−0.0076 (12)
C130.0881 (15)0.0816 (14)0.0746 (13)−0.0110 (12)0.0358 (12)−0.0003 (11)
C140.0770 (13)0.0800 (13)0.0680 (12)0.0054 (11)0.0281 (10)0.0050 (11)
C150.0619 (12)0.0796 (12)0.0680 (12)0.0011 (10)0.0291 (10)−0.0036 (11)
Geometric parameters (Å, °) top
N1—C31.363 (2)C6—C71.394 (2)
N1—C11.444 (2)C6—C91.449 (3)
N1—C21.447 (2)C7—C81.361 (2)
N2—C91.274 (2)C7—H70.9300
N2—C101.411 (2)C8—H80.9300
C1—H1A0.9600C9—H90.9300
C1—H1B0.9600C10—C151.388 (3)
C1—H1C0.9600C10—C111.388 (3)
C2—H2A0.9600C11—C121.375 (3)
C2—H2B0.9600C11—H110.9300
C2—H2C0.9600C12—C131.375 (3)
C3—C41.403 (2)C12—H120.9300
C3—C81.407 (2)C13—C141.375 (3)
C4—C51.364 (2)C13—H130.9300
C4—H40.9300C14—C151.370 (3)
C5—C61.389 (2)C14—H140.9300
C5—H50.9300C15—H150.9300
C3—N1—C1121.18 (15)C8—C7—C6121.63 (16)
C3—N1—C2121.17 (16)C8—C7—H7119.2
C1—N1—C2117.39 (17)C6—C7—H7119.2
C9—N2—C10118.88 (16)C7—C8—C3121.55 (16)
N1—C1—H1A109.5C7—C8—H8119.2
N1—C1—H1B109.5C3—C8—H8119.2
H1A—C1—H1B109.5N2—C9—C6124.65 (17)
N1—C1—H1C109.5N2—C9—H9117.7
H1A—C1—H1C109.5C6—C9—H9117.7
H1B—C1—H1C109.5C15—C10—C11118.49 (18)
N1—C2—H2A109.5C15—C10—N2118.89 (16)
N1—C2—H2B109.5C11—C10—N2122.57 (18)
H2A—C2—H2B109.5C12—C11—C10120.17 (19)
N1—C2—H2C109.5C12—C11—H11119.9
H2A—C2—H2C109.5C10—C11—H11119.9
H2B—C2—H2C109.5C13—C12—C11120.63 (19)
N1—C3—C4121.86 (16)C13—C12—H12119.7
N1—C3—C8121.37 (16)C11—C12—H12119.7
C4—C3—C8116.77 (17)C12—C13—C14119.64 (19)
C5—C4—C3120.70 (16)C12—C13—H13120.2
C5—C4—H4119.7C14—C13—H13120.2
C3—C4—H4119.7C15—C14—C13120.05 (19)
C4—C5—C6122.56 (16)C15—C14—H14120.0
C4—C5—H5118.7C13—C14—H14120.0
C6—C5—H5118.7C14—C15—C10121.00 (18)
C5—C6—C7116.79 (17)C14—C15—H15119.5
C5—C6—C9120.79 (17)C10—C15—H15119.5
C7—C6—C9122.42 (17)
C1—N1—C3—C4−175.41 (16)C10—N2—C9—C6−176.70 (15)
C2—N1—C3—C4−1.3 (3)C5—C6—C9—N2−170.32 (18)
C1—N1—C3—C84.7 (3)C7—C6—C9—N29.2 (3)
C2—N1—C3—C8178.74 (17)C9—N2—C10—C15−137.72 (18)
N1—C3—C4—C5−179.28 (17)C9—N2—C10—C1144.8 (2)
C8—C3—C4—C50.6 (3)C15—C10—C11—C120.7 (3)
C3—C4—C5—C6−0.7 (3)N2—C10—C11—C12178.17 (16)
C4—C5—C6—C70.5 (3)C10—C11—C12—C130.2 (3)
C4—C5—C6—C9−179.94 (17)C11—C12—C13—C14−0.8 (3)
C5—C6—C7—C8−0.3 (3)C12—C13—C14—C150.4 (3)
C9—C6—C7—C8−179.89 (17)C13—C14—C15—C100.5 (3)
C6—C7—C8—C30.4 (3)C11—C10—C15—C14−1.0 (3)
N1—C3—C8—C7179.43 (16)N2—C10—C15—C14−178.61 (16)
C4—C3—C8—C7−0.5 (3)
Acknowledgements top

The authors thank Mr Zhi-Hua Mao, Sichuan University, for the X-ray data collection.

references
References top

Ahmet, M. T., Silver, J. & Houlton, A. (1994). Acta Cryst. C50, 1814–1818.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.

Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384–387.

Gabe, E. J., White, P. S. & Enright, G. D. (1993). DIFRAC. American Crystallographic Association, Pittsburgh Meeting, Abstract PA 104.

Hodnett, E. M. & Dunn, W. J. (1970). J. Med. Chem. 13, 768–770.

Nakai, H., Shiro, M., Emuzi, K., Sakata, S. & Kubota, T. (1976). Acta Cryst. B32, 1827–1833.

Nyarku, S. K. & Mavuso, E. (1998). S. Afr. J. Chem. 51, 168–172.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Tang, C. W. & Vanslyke, S. A. (1987). Appl. Phys. Lett. 51, 913–915.

Wang, Q. & Wang, D.-Q. (2007). Acta Cryst. E63, o4838.

Wang, Q. & Wang, D.-Q. (2008). Acta Cryst. E64, o51.

Yu, G., LIU, Y. Q. & Song, Y. R. (2001). Synth. Met. 117, 211–214.