4-Eth­oxy-N-(3-phenyl­prop-2-enyl­idene)aniline

Sun, Y.-Y.; Wang, Q.; Wang, D.-Q.

doi:10.1107/S1600536808014050

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1094

doi:10.1107/S1600536808014050

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4-Ethoxy-N-(3-phenylprop-2-enylidene)aniline

Yu-Ying Sun,^a Qiang Wang ^b and Da-Qi Wang ^b ^*

^aAnalytical and Testing Center of Beihua Univerisity, Jilin 132031, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: wdq4899@163.com

(Received 23 March 2008; accepted 10 May 2008; online 17 May 2008)

The title compound, C₁₇H₁₇NO, was prepared by the condensation of cinnamaldehyde with p-phenetidine in ethanol. The prop-2-enylidene group exhibits an E configuration at the N=C and C=C double bonds, with C—N—C—C and C—C—C—C torsion angles of −179.9 (3) and −175.9 (3)°, respectively. The prop-2-enylidene group is not strictly planar [maximum deviation = 0.054 (4) Å] and forms dihedral angles of 28.0 (3) and 34.9 (3)° with the attached aromatic rings.

Related literature

For general background, see: Lindoy et al. (1976 ).

Experimental

Crystal data

C₁₇H₁₇NO
M_r = 251.32
Monoclinic, P 2₁ /c
a = 31.12 (2) Å
b = 7.198 (6) Å
c = 6.315 (5) Å
β = 95.822 (10)°
V = 1407.3 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 298 (2) K
0.52 × 0.47 × 0.30 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.963, T_max = 0.978
6773 measured reflections
2449 independent reflections
1165 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.076
wR(F²) = 0.221
S = 1.02
2449 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.35 e Å⁻³

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 I, global. DOI: 10.1107/S1600536808014050/rz2203sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808014050/rz2203Isup2.hkl

checkCIF report

Comment top

Schiff bases are known to be important due to their applications in the synthesis of dyes, liquid crystals and as powerful corrosion inhibitors. Furthermore, they are involved in the mechanisms of many biochemical processes (Lindoy et al., 1976). We report here the synthesis and crystal structure of the title compound, a new Schiff base compound.

The molecular structure of the title compound is shown in Fig. 1. The prop-2-enylidene group exhibits an E configuration at the N1═C1 (1.276 (4) Å) and C2═C3 (1.321 (5) Å) double bonds, with C10-N1-C1-C2 and C1-C2-C3-C4 torsion angles of -179.9 (3)° and -175.9 (3)° respectively. This group is not strictly planar (maximum deviation 0.054 (4) Å for atom C2) and forms dihedral angles of 28.0 (3) and 34.9 (3)° with the attached aromatic rings. The crystal structure (Fig. 2) is stabilized only by van der Waals interactions.

Related literature top

For general background, see: Lindoy et al. (1976).

Experimental top

Cinnamaldehyde (5 mmol, 660.8 mg) in absolute ethanol (10 ml) was added dropwise to an absolute ethanol solution (10 ml) of p-phenetidine (5 mmol, 690.7 mg). The mixture was heated under reflux with stirring for 4 h and then filtered. The resulting clear solution was kept at room temperature for one week, after which large pale-yellow block-shaped crystals of the title compound suitable for X-ray diffraction analysis were obtained.

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 molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Perspective view of the crystal packing of the title compound along the c axis. Hydrogen atoms are omitted for clarity.

4-Ethoxy-N-(3-phenylprop-2-enylidene)aniline top

Crystal data top

C₁₇H₁₇NO	F(000) = 536
M_r = 251.32	D_x = 1.186 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1073 reflections
a = 31.12 (2) Å	θ = 2.6–23.2°
b = 7.198 (6) Å	µ = 0.07 mm⁻¹
c = 6.315 (5) Å	T = 298 K
β = 95.822 (10)°	Block, pale-yellow
V = 1407.3 (19) Å³	0.52 × 0.47 × 0.30 mm
Z = 4

Data collection top

Siemens SMART CCD area-detector diffractometer	2449 independent reflections
Radiation source: fine-focus sealed tube	1165 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −36→37
T_min = 0.963, T_max = 0.978	k = −8→7
6773 measured reflections	l = −7→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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.221	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0854P)² + 0.6793P] where P = (F_o² + 2F_c²)/3
2449 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₇H₁₇NO	V = 1407.3 (19) Å³
M_r = 251.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 31.12 (2) Å	µ = 0.07 mm⁻¹
b = 7.198 (6) Å	T = 298 K
c = 6.315 (5) Å	0.52 × 0.47 × 0.30 mm
β = 95.822 (10)°

Data collection top

Siemens SMART CCD area-detector diffractometer	2449 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1165 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.978	R_int = 0.072
6773 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.076	0 restraints
wR(F²) = 0.221	H-atom parameters constrained
S = 1.02	Δρ_max = 0.17 e Å⁻³
2449 reflections	Δρ_min = −0.35 e Å⁻³
172 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	0.26172 (9)	0.5173 (4)	0.8270 (5)	0.0442 (8)
O1	0.09317 (8)	0.5040 (4)	1.0522 (4)	0.0547 (8)
C1	0.27064 (12)	0.5295 (5)	0.6347 (6)	0.0434 (10)
H1	0.2481	0.5343	0.5262	0.052*
C2	0.31443 (12)	0.5359 (5)	0.5801 (6)	0.0452 (10)
H2	0.3364	0.5506	0.6903	0.054*
C3	0.32565 (12)	0.5225 (5)	0.3845 (6)	0.0450 (10)
H3	0.3033	0.5162	0.2750	0.054*
C4	0.36937 (11)	0.5166 (5)	0.3235 (6)	0.0410 (10)
C5	0.37720 (13)	0.4321 (6)	0.1308 (6)	0.0503 (11)
H5	0.3542	0.3854	0.0408	0.060*
C6	0.41851 (14)	0.4178 (6)	0.0742 (6)	0.0588 (12)
H6	0.4232	0.3602	−0.0532	0.071*
C7	0.45320 (14)	0.4877 (6)	0.2034 (7)	0.0608 (12)
H7	0.4811	0.4772	0.1643	0.073*
C8	0.44578 (12)	0.5730 (6)	0.3907 (6)	0.0537 (11)
H8	0.4688	0.6214	0.4788	0.064*
C9	0.40471 (11)	0.5873 (5)	0.4489 (6)	0.0454 (10)
H9	0.4004	0.6462	0.5762	0.054*
C10	0.21832 (10)	0.5112 (5)	0.8727 (5)	0.0353 (9)
C11	0.20976 (11)	0.4159 (5)	1.0554 (5)	0.0387 (9)
H11	0.2323	0.3578	1.1382	0.046*
C12	0.16848 (11)	0.4062 (5)	1.1158 (6)	0.0431 (10)
H12	0.1633	0.3379	1.2357	0.052*
C13	0.13480 (11)	0.4965 (5)	1.0008 (6)	0.0390 (9)
C14	0.14323 (11)	0.5926 (5)	0.8180 (6)	0.0414 (9)
H14	0.1208	0.6528	0.7370	0.050*
C15	0.18419 (11)	0.5995 (5)	0.7561 (5)	0.0398 (9)
H15	0.1891	0.6647	0.6337	0.048*
C16	0.08474 (13)	0.4248 (7)	1.2501 (7)	0.0698 (14)
H16A	0.1052	0.4718	1.3637	0.084*
H16B	0.0876	0.2907	1.2451	0.084*
C17	0.03980 (16)	0.4766 (9)	1.2899 (9)	0.119 (2)
H17A	0.0333	0.4245	1.4229	0.179*
H17B	0.0198	0.4293	1.1769	0.179*
H17C	0.0374	0.6095	1.2955	0.179*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.048 (2)	0.048 (2)	0.0374 (19)	0.0020 (15)	0.0063 (14)	−0.0004 (16)
O1	0.0566 (18)	0.057 (2)	0.0525 (18)	0.0042 (13)	0.0146 (13)	0.0112 (15)
C1	0.047 (2)	0.039 (3)	0.044 (2)	0.0006 (17)	0.0020 (18)	−0.0006 (19)
C2	0.050 (2)	0.045 (3)	0.041 (2)	−0.0010 (18)	0.0020 (18)	0.0020 (19)
C3	0.049 (2)	0.042 (3)	0.042 (2)	−0.0004 (18)	−0.0036 (18)	0.0033 (19)
C4	0.051 (2)	0.035 (2)	0.037 (2)	0.0016 (17)	0.0039 (18)	0.0060 (18)
C5	0.064 (3)	0.049 (3)	0.037 (2)	−0.003 (2)	0.003 (2)	−0.001 (2)
C6	0.084 (3)	0.052 (3)	0.043 (3)	0.008 (2)	0.020 (2)	0.001 (2)
C7	0.059 (3)	0.068 (3)	0.057 (3)	0.009 (2)	0.016 (2)	0.011 (3)
C8	0.046 (2)	0.063 (3)	0.052 (3)	0.0026 (19)	0.0015 (19)	0.001 (2)
C9	0.046 (2)	0.046 (3)	0.044 (2)	0.0013 (18)	0.0048 (18)	−0.0039 (19)
C10	0.040 (2)	0.028 (2)	0.037 (2)	0.0033 (15)	0.0005 (16)	−0.0010 (17)
C11	0.046 (2)	0.038 (2)	0.031 (2)	0.0041 (16)	0.0019 (16)	0.0030 (17)
C12	0.057 (3)	0.036 (2)	0.036 (2)	0.0005 (18)	0.0066 (18)	0.0039 (18)
C13	0.041 (2)	0.035 (2)	0.042 (2)	−0.0028 (17)	0.0089 (18)	−0.0037 (18)
C14	0.050 (2)	0.035 (2)	0.039 (2)	0.0034 (17)	0.0006 (17)	−0.0016 (18)
C15	0.059 (2)	0.030 (2)	0.031 (2)	0.0018 (17)	0.0074 (17)	0.0044 (17)
C16	0.064 (3)	0.083 (4)	0.066 (3)	−0.001 (2)	0.022 (2)	0.016 (3)
C17	0.083 (4)	0.168 (7)	0.116 (5)	0.020 (4)	0.057 (3)	0.049 (5)

Geometric parameters (Å, º) top

N1—C1	1.276 (4)	C8—H8	0.9300
N1—C10	1.410 (4)	C9—H9	0.9300
O1—C13	1.368 (4)	C10—C15	1.384 (5)
O1—C16	1.422 (4)	C10—C11	1.391 (4)
C1—C2	1.440 (5)	C11—C12	1.378 (4)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.321 (5)	C12—C13	1.376 (5)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.452 (5)	C13—C14	1.393 (5)
C3—H3	0.9300	C14—C15	1.372 (4)
C4—C9	1.386 (5)	C14—H14	0.9300
C4—C5	1.404 (5)	C15—H15	0.9300
C5—C6	1.373 (5)	C16—C17	1.493 (6)
C5—H5	0.9300	C16—H16A	0.9700
C6—C7	1.380 (6)	C16—H16B	0.9700
C6—H6	0.9300	C17—H17A	0.9600
C7—C8	1.373 (5)	C17—H17B	0.9600
C7—H7	0.9300	C17—H17C	0.9600
C8—C9	1.369 (5)

C1—N1—C10	120.1 (3)	C15—C10—N1	125.2 (3)
C13—O1—C16	117.2 (3)	C11—C10—N1	117.0 (3)
N1—C1—C2	122.2 (3)	C12—C11—C10	121.1 (3)
N1—C1—H1	118.9	C12—C11—H11	119.4
C2—C1—H1	118.9	C10—C11—H11	119.4
C3—C2—C1	124.6 (4)	C13—C12—C11	120.7 (3)
C3—C2—H2	117.7	C13—C12—H12	119.6
C1—C2—H2	117.7	C11—C12—H12	119.6
C2—C3—C4	126.4 (4)	O1—C13—C12	125.6 (3)
C2—C3—H3	116.8	O1—C13—C14	116.1 (3)
C4—C3—H3	116.8	C12—C13—C14	118.3 (3)
C9—C4—C5	117.2 (3)	C15—C14—C13	120.9 (3)
C9—C4—C3	123.3 (3)	C15—C14—H14	119.6
C5—C4—C3	119.5 (3)	C13—C14—H14	119.6
C6—C5—C4	120.5 (4)	C14—C15—C10	121.1 (3)
C6—C5—H5	119.8	C14—C15—H15	119.4
C4—C5—H5	119.8	C10—C15—H15	119.4
C5—C6—C7	121.1 (4)	O1—C16—C17	107.9 (4)
C5—C6—H6	119.5	O1—C16—H16A	110.1
C7—C6—H6	119.5	C17—C16—H16A	110.1
C8—C7—C6	118.8 (4)	O1—C16—H16B	110.1
C8—C7—H7	120.6	C17—C16—H16B	110.1
C6—C7—H7	120.6	H16A—C16—H16B	108.4
C9—C8—C7	120.6 (4)	C16—C17—H17A	109.5
C9—C8—H8	119.7	C16—C17—H17B	109.5
C7—C8—H8	119.7	H17A—C17—H17B	109.5
C8—C9—C4	121.8 (4)	C16—C17—H17C	109.5
C8—C9—H9	119.1	H17A—C17—H17C	109.5
C4—C9—H9	119.1	H17B—C17—H17C	109.5
C15—C10—C11	117.8 (3)

C10—N1—C1—C2	−179.9 (3)	C1—N1—C10—C11	151.0 (3)
N1—C1—C2—C3	170.1 (4)	C15—C10—C11—C12	1.4 (5)
C1—C2—C3—C4	−175.9 (3)	N1—C10—C11—C12	178.5 (3)
C2—C3—C4—C9	−23.3 (6)	C10—C11—C12—C13	−2.4 (5)
C2—C3—C4—C5	155.2 (4)	C16—O1—C13—C12	5.5 (5)
C9—C4—C5—C6	1.4 (5)	C16—O1—C13—C14	−173.2 (3)
C3—C4—C5—C6	−177.2 (4)	C11—C12—C13—O1	−176.5 (3)
C4—C5—C6—C7	−0.7 (6)	C11—C12—C13—C14	2.1 (5)
C5—C6—C7—C8	−0.2 (6)	O1—C13—C14—C15	177.7 (3)
C6—C7—C8—C9	0.4 (6)	C12—C13—C14—C15	−1.0 (5)
C7—C8—C9—C4	0.3 (6)	C13—C14—C15—C10	0.1 (5)
C5—C4—C9—C8	−1.2 (5)	C11—C10—C15—C14	−0.3 (5)
C3—C4—C9—C8	177.3 (4)	N1—C10—C15—C14	−177.1 (3)
C1—N1—C10—C15	−32.2 (5)	C13—O1—C16—C17	170.5 (4)

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇NO
M_r	251.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	31.12 (2), 7.198 (6), 6.315 (5)
β (°)	95.822 (10)
V (Å³)	1407.3 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.52 × 0.47 × 0.30

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.963, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	6773, 2449, 1165
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.076, 0.221, 1.02
No. of reflections	2449
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.35

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

Acknowledgements

The authors acknowledge the financial support of the Shandong Province Science Foundation and the State Key Laboratory of Crystalline Materials, Shandong University, People's Republic of China.

References

Lindoy, L. F., Lip, H. C., Power, L. F. & Rea, T. H. (1976). Inorg. Chem. 15, 1724–1727. CrossRef CAS Web of Science 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
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar