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

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

doi:10.1107/S1600536809003791

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o506

doi:10.1107/S1600536809003791

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

Lei Zheng,^a Xiu-juan Yin,^a Cong-ling Yang,^a Ying Li ^a and Shu-fan Yin ^a ^*

^aCollege of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
^*Correspondence e-mail: chuandayouji217@163.com

(Received 13 January 2009; accepted 1 February 2009; online 11 February 2009)

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)°.

Related literature

For the physical properties and physiological activity of Schiff bases, 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

Crystal data

C₁₅H₁₆N₂
M_r = 224.30
Monoclinic, P 2₁ /c
a = 9.441 (4) Å
b = 8.356 (3) Å
c = 17.245 (5) Å
β = 110.97 (2)°
V = 1270.4 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 292 (2) K
0.52 × 0.48 × 0.46 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
3023 measured reflections
2328 independent reflections
1336 reflections with I > 2σ(I)
R_int = 0.012
3 standard reflections every 200 reflections intensity decay: 1.8%

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.150
S = 1.02
2328 reflections
157 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: DIFRAC (Gabe et al., 1993 ); cell refinement: NRCVAX (Gabe et al., 1989 ); data reduction: NRCVAX; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003791/pv2134sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809003791/pv2134Isup2.hkl

checkCIF report

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.

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

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

C₁₅H₁₆N₂	F(000) = 480
M_r = 224.30	D_x = 1.173 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 20 reflections
a = 9.441 (4) Å	θ = 4.4–7.1°
b = 8.356 (3) Å	µ = 0.07 mm⁻¹
c = 17.245 (5) Å	T = 292 K
β = 110.97 (2)°	Block, colourless
V = 1270.4 (8) Å³	0.52 × 0.48 × 0.46 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.012
Radiation source: fine-focus sealed tube	θ_max = 25.5°, θ_min = 2.3°
Graphite monochromator	h = −11→11
ω/2θ scans	k = −10→0
3023 measured reflections	l = −20→10
2328 independent reflections	3 standard reflections every 200 reflections
1336 reflections with I > 2σ(I)	intensity decay: 1.8%

Refinement top

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)] = 0.047	H-atom parameters constrained
wR(F²) = 0.150	w = 1/[σ²(F_o²) + (0.0913P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2328 reflections	Δρ_max = 0.13 e Å⁻³
157 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.032 (10)

Crystal data top

C₁₅H₁₆N₂	V = 1270.4 (8) Å³
M_r = 224.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.441 (4) Å	µ = 0.07 mm⁻¹
b = 8.356 (3) Å	T = 292 K
c = 17.245 (5) Å	0.52 × 0.48 × 0.46 mm
β = 110.97 (2)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.012
3023 measured reflections	3 standard reflections every 200 reflections
2328 independent reflections	intensity decay: 1.8%
1336 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.02	Δρ_max = 0.13 e Å⁻³
2328 reflections	Δρ_min = −0.14 e Å⁻³
157 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 > 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

	x	y	z	U_iso*/U_eq
N1	0.30901 (17)	1.50607 (18)	−0.07311 (10)	0.0722 (5)
N2	0.28787 (18)	0.86291 (19)	0.13032 (9)	0.0668 (5)
C1	0.3837 (2)	1.4806 (2)	−0.13194 (12)	0.0815 (6)
H1A	0.4831	1.4372	−0.1037	0.122*
H1B	0.3924	1.5807	−0.1572	0.122*
H1C	0.3254	1.4071	−0.1740	0.122*
C2	0.2456 (3)	1.6630 (2)	−0.07117 (15)	0.0907 (7)
H2A	0.1369	1.6571	−0.0944	0.136*
H2B	0.2810	1.7363	−0.1031	0.136*
H2C	0.2768	1.6997	−0.0148	0.136*
C3	0.28724 (19)	1.3833 (2)	−0.02654 (11)	0.0587 (5)
C4	0.2055 (2)	1.4036 (2)	0.02656 (12)	0.0687 (5)
H4	0.1636	1.5029	0.0300	0.082*
C5	0.1867 (2)	1.2792 (2)	0.07319 (12)	0.0686 (5)
H5	0.1329	1.2965	0.1082	0.082*
C6	0.2449 (2)	1.1275 (2)	0.07036 (11)	0.0616 (5)
C7	0.3258 (2)	1.1071 (2)	0.01746 (10)	0.0636 (5)
H7	0.3669	1.0073	0.0142	0.076*
C8	0.3462 (2)	1.2297 (2)	−0.02946 (11)	0.0625 (5)
H8	0.4004	1.2115	−0.0643	0.075*
C9	0.2222 (2)	0.9985 (2)	0.12090 (11)	0.0681 (5)
H9	0.1550	1.0160	0.1484	0.082*
C10	0.2496 (2)	0.7447 (2)	0.17785 (11)	0.0619 (5)
C11	0.1006 (2)	0.7114 (2)	0.16925 (12)	0.0715 (6)
H11	0.0217	0.7702	0.1321	0.086*
C12	0.0694 (2)	0.5918 (3)	0.21553 (13)	0.0795 (6)
H12	−0.0307	0.5700	0.2093	0.095*
C13	0.1848 (3)	0.5041 (2)	0.27093 (13)	0.0796 (6)
H13	0.1629	0.4243	0.3025	0.096*
C14	0.3326 (2)	0.5352 (2)	0.27936 (12)	0.0744 (6)
H14	0.4110	0.4757	0.3165	0.089*
C15	0.3645 (2)	0.6536 (2)	0.23315 (11)	0.0682 (5)
H15	0.4648	0.6733	0.2389	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0775 (11)	0.0677 (10)	0.0723 (11)	0.0087 (8)	0.0278 (9)	0.0044 (8)
N2	0.0681 (10)	0.0769 (11)	0.0590 (9)	0.0019 (8)	0.0270 (8)	−0.0015 (8)
C1	0.0882 (14)	0.0911 (14)	0.0695 (12)	−0.0005 (11)	0.0338 (11)	0.0092 (11)
C2	0.0945 (16)	0.0719 (13)	0.1018 (16)	0.0086 (11)	0.0305 (14)	0.0059 (12)
C3	0.0538 (10)	0.0656 (11)	0.0530 (10)	−0.0001 (8)	0.0146 (8)	−0.0077 (9)
C4	0.0696 (12)	0.0667 (11)	0.0716 (12)	0.0094 (9)	0.0276 (10)	−0.0083 (10)
C5	0.0684 (12)	0.0816 (14)	0.0637 (11)	0.0060 (10)	0.0333 (10)	−0.0109 (10)
C6	0.0620 (11)	0.0713 (12)	0.0535 (10)	0.0026 (9)	0.0231 (9)	−0.0057 (9)
C7	0.0682 (12)	0.0637 (11)	0.0630 (11)	0.0070 (9)	0.0285 (10)	−0.0066 (9)
C8	0.0669 (12)	0.0682 (12)	0.0580 (11)	0.0063 (9)	0.0290 (9)	−0.0048 (9)
C9	0.0657 (12)	0.0836 (14)	0.0594 (11)	0.0019 (10)	0.0278 (9)	−0.0064 (10)
C10	0.0642 (12)	0.0724 (11)	0.0528 (10)	−0.0030 (10)	0.0255 (9)	−0.0095 (9)
C11	0.0607 (12)	0.0852 (14)	0.0656 (12)	−0.0022 (10)	0.0191 (10)	−0.0030 (11)
C12	0.0657 (12)	0.0961 (15)	0.0779 (13)	−0.0151 (11)	0.0271 (11)	−0.0076 (12)
C13	0.0881 (15)	0.0816 (14)	0.0746 (13)	−0.0110 (12)	0.0358 (12)	−0.0003 (11)
C14	0.0770 (13)	0.0800 (13)	0.0680 (12)	0.0054 (11)	0.0281 (10)	0.0050 (11)
C15	0.0619 (12)	0.0796 (12)	0.0680 (12)	0.0011 (10)	0.0291 (10)	−0.0036 (11)

Geometric parameters (Å, º) top

N1—C3	1.363 (2)	C6—C7	1.394 (2)
N1—C1	1.444 (2)	C6—C9	1.449 (3)
N1—C2	1.447 (2)	C7—C8	1.361 (2)
N2—C9	1.274 (2)	C7—H7	0.9300
N2—C10	1.411 (2)	C8—H8	0.9300
C1—H1A	0.9600	C9—H9	0.9300
C1—H1B	0.9600	C10—C15	1.388 (3)
C1—H1C	0.9600	C10—C11	1.388 (3)
C2—H2A	0.9600	C11—C12	1.375 (3)
C2—H2B	0.9600	C11—H11	0.9300
C2—H2C	0.9600	C12—C13	1.375 (3)
C3—C4	1.403 (2)	C12—H12	0.9300
C3—C8	1.407 (2)	C13—C14	1.375 (3)
C4—C5	1.364 (2)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.370 (3)
C5—C6	1.389 (2)	C14—H14	0.9300
C5—H5	0.9300	C15—H15	0.9300

C3—N1—C1	121.18 (15)	C8—C7—C6	121.63 (16)
C3—N1—C2	121.17 (16)	C8—C7—H7	119.2
C1—N1—C2	117.39 (17)	C6—C7—H7	119.2
C9—N2—C10	118.88 (16)	C7—C8—C3	121.55 (16)
N1—C1—H1A	109.5	C7—C8—H8	119.2
N1—C1—H1B	109.5	C3—C8—H8	119.2
H1A—C1—H1B	109.5	N2—C9—C6	124.65 (17)
N1—C1—H1C	109.5	N2—C9—H9	117.7
H1A—C1—H1C	109.5	C6—C9—H9	117.7
H1B—C1—H1C	109.5	C15—C10—C11	118.49 (18)
N1—C2—H2A	109.5	C15—C10—N2	118.89 (16)
N1—C2—H2B	109.5	C11—C10—N2	122.57 (18)
H2A—C2—H2B	109.5	C12—C11—C10	120.17 (19)
N1—C2—H2C	109.5	C12—C11—H11	119.9
H2A—C2—H2C	109.5	C10—C11—H11	119.9
H2B—C2—H2C	109.5	C13—C12—C11	120.63 (19)
N1—C3—C4	121.86 (16)	C13—C12—H12	119.7
N1—C3—C8	121.37 (16)	C11—C12—H12	119.7
C4—C3—C8	116.77 (17)	C12—C13—C14	119.64 (19)
C5—C4—C3	120.70 (16)	C12—C13—H13	120.2
C5—C4—H4	119.7	C14—C13—H13	120.2
C3—C4—H4	119.7	C15—C14—C13	120.05 (19)
C4—C5—C6	122.56 (16)	C15—C14—H14	120.0
C4—C5—H5	118.7	C13—C14—H14	120.0
C6—C5—H5	118.7	C14—C15—C10	121.00 (18)
C5—C6—C7	116.79 (17)	C14—C15—H15	119.5
C5—C6—C9	120.79 (17)	C10—C15—H15	119.5
C7—C6—C9	122.42 (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—C8	4.7 (3)	C7—C6—C9—N2	9.2 (3)
C2—N1—C3—C8	178.74 (17)	C9—N2—C10—C15	−137.72 (18)
N1—C3—C4—C5	−179.28 (17)	C9—N2—C10—C11	44.8 (2)
C8—C3—C4—C5	0.6 (3)	C15—C10—C11—C12	0.7 (3)
C3—C4—C5—C6	−0.7 (3)	N2—C10—C11—C12	178.17 (16)
C4—C5—C6—C7	0.5 (3)	C10—C11—C12—C13	0.2 (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—C15	0.4 (3)
C9—C6—C7—C8	−179.89 (17)	C13—C14—C15—C10	0.5 (3)
C6—C7—C8—C3	0.4 (3)	C11—C10—C15—C14	−1.0 (3)
N1—C3—C8—C7	179.43 (16)	N2—C10—C15—C14	−178.61 (16)
C4—C3—C8—C7	−0.5 (3)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆N₂
M_r	224.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	292
a, b, c (Å)	9.441 (4), 8.356 (3), 17.245 (5)
β (°)	110.97 (2)
V (Å³)	1270.4 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.52 × 0.48 × 0.46

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3023, 2328, 1336
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.605

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.150, 1.02
No. of reflections	2328
No. of parameters	157
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.14

Computer programs: DIFRAC (Gabe et al., 1993), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia,1997).

Acknowledgements

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

References

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